Once again, I've been asked to write. 

I had made the very questionable decision to be open to buying a sailboat. This was not as straightforward as one might think and required a lot of painful soul searching.

There's an aspect to this that continues to feel so very wrong, as if I'm committing some kind of egregious selfish sin. I've never done anything like this before. My entire life has been spent in the service of others often at great cost and harm to myself. There were the decades dealing with the Nightmare from which, contrary to what I had thought, I've not recovered and probably never will.   

Now I am the last member of my immediate family alive. Of others I've tried to be good for, some are dead, others are just gone. I am close to as alone as it gets. There's no one left that depends on me. Still, compulsively, I try to find ways where I can be of some service. But I know that's not an answer either. There's just no point to me. I'm not sure that there ever was. There is this powerful sense that doing anything "just for me" is just wrong. 

There's also this strong sense that it's all too frivolous and will take away from the Project. I should continue just sitting here in this office slaving away. I am work. I make everything work.

But the Project I've been working on for so long like some kind of beaver afraid to stop working for fear I'll die if I don't work, is not going well. It's too big and I continue to be on this death march trying so hard to keep up with the relentless changes that occur at such a rate I struggle to keep up. There are very difficult to reproduce bugs that I still have no clue why they are happening. Still I persist but it makes no sense. If it becomes operational I'll be forced to stop all travel because i'll be tied to the servers and doing endless customer support. I'll either have to find investors or better yet some partner organization, then this platform and the companion app I've written for it might have a chance ... but that would mean continuing the grind for more years on end and I just don't know if I have it in me any more especially if it's not of real benefit to anyone. Making money by itself has never been that much of a motivator for me. Making money so I have the means to help keep someone alive or off the streets, on the other hand, is an extreme motivator. But still I work even if there is no money involved. I often work for free. But I've come to understand that even that needs to be examined. This reminds me of a conversation I recently had with a friend who has a work ethic rivaling my own. She said, "My identity is too tied to the work I do." That caused me to pause as it rang true for myself.  

Over the last several years I've learned to "cultivate the watcher" as they say. This means when I am aware that I feel something, especially something uncomfortable, to pause and as nonjudgementally as possible just be curious about that feeling. To "watch" it and not react to it, in effect. It's terribly difficult not to look away and absolutely ego-defeating, but that's kind of the point. The ego that has served me for a lifetime is no longer serving me and has to be sacrificed. It's a slow process but with repetition one learns to recognize the feeling and separate it from the story one makes up explaining it. "If I don't work constantly, bad bad things will happen like they always have." is the story I have used to explain this feeling of terror. But the story makes no sense. If I stop, the world won't end. It'll just feel to me like it will.  

I mentioned all this to my best friend, Duncan, who is one of the biggest reasons I am still standing. Duncan is extremely wise, like the older brother I never had, and suggested that maybe all these feelings of "wrong" that are bubbling up when I consider buying a boat just for myself need to be examined. Maybe the boat is the next part of the Work(tm). 

It took me a while but eventually that began to make sense to me. Yes, maybe this is part of the Work(tm).

So I grit my teeth and continued to be open to buying a boat watching this cacophony of uncomfortable feelings arise. 

I say "open to" because it was clear to me this was going to be a process of learning and waiting until what appeared to be the "right" boat came along. I had no timeline. I had no real preconceptions. I was just "open". I was also aware that I might not ever find a boat, but even so I would learn quite a bit by going through the process.

I didn't even know what kind of boat to get.

I wasn't doing this for all the typical reasons people buy boats. There are no happy thoughts. There are no delusions of tropical paradises, that is unless I'm there fixing my boat. I want to do this to go through the process. I want the problems. I want the work because I want to learn so I can be more effective when I crew. Why do I want to do all this? I really don't know. It feels like something I need to do. It draws me in. I feel better on a sailboat so maybe I should do that more.

During that first crossing on AraVilla, because the topic of boats came up so often, I started a habit of browsing boat ads to gain a feel for the different kinds of sailboats out there. Whenever the opportunity arose, I would ask questions about what brands were good and what brands should be avoided. 

Dana's friend Terry, who is a very experienced sailor and one of the kindest human beings I've ever met, advised me at one point not to pay so much attention to brands but instead features.  

"Don't pay so much attention to brands. Pay attention to the features and build quality of a specific boat."

It would take me some years to understand the wisdom of this advice and it would have an outsized effect later on. 

Because of my relative inexperience I thought I should follow my own advice that I give when people get into motorcycling. "Get a small inexpensive bike to learn on." 

So I thought maybe what I should do is buy a coastal cruiser and just sail around the bay. That would be a safe answer. 

To this Duncan said, "Yermo! I know you. The first thing you're going to want to do is take it offshore. Get yourself an offshore capable boat."

He was right, of course. I am the guy that takes a K100RS up jeep trails where no fully loaded street bike should go. 

 

Before going up this jeep trail back in 2010 I did literally say to someone, "There's no way I'm going up there. I don't have a death wish." So of course, I went up. 

Ok, so it will be an offshore boat. This makes things much more serious. But then it dawned on me that the primary reason I was getting a boat was so that I could learn how to be a much better crewmember on the crossing to the Med with Dana on his 46 catamaran. 

So there's an aspect of work and service to this after all. 

Catamarans are sailed a bit differently than monohulls, but the similarities far outweigh the differences. I pondered maybe I should get a monohull in the same general class as Dana's catamaran. 

I continued looking at boats and slowly started coming up with a list of requirements and nice to haves. 

The closest body of water to me is the Chesapeake Bay. It's surprisingly shallow so having a boat with a deep keel would be extremely limiting. So having something I could take in shallow water was a requirement. Tabasco had something called a swing keel. It can be pulled up when in shallower water or dropped down when in deeper water. Deep keels help when sailing more towards the wind which is beneficial since it seems that the wind is always coming exactly from where you want to go. 

So I thought getting something with the swing keel would be nice. 

In my circle of friends, there are a number of us with health problems. This is one of the reasons I never go on a boat without a bathroom. If you have two people with issues, having only one bathroom (a.k.a. head) can be Bad(tm). So another hard requirement for me was that the boat should have two heads. The smallest boats I saw with two heads were around 38 feet. The largest boats I could find that could float in 5 feet of water, which would allow me to visit the majority of places in the Chesapeake, were around 44 feet. 

44 feet seemed like a lot of boat. 

I joined a bunch of Facebook sailing groups and started reading opinions from all kinds of people. i read articles from boat surveyors about common problems with various brands. The problem is that the experiences of others are often from a context that's different from your own. So it's really hard to tell what issues that people warn you about are really common and what issues are unlikely. There's a lot of talk about keels online. There are these huge bolts, keel bolts, that as the name implies hold the keel. If you believe what you read online keels falling off these days is super common. So it's really hard to tell what to pay attention to and what not to.

There were, however, ideas that would get repeated from many sources. Greg, owner of the Ontario 32, at one point said he expected boats made in the 80's and early 90's to still be around decades after boats built after 2000 are no longer serviceable. As technology and production capabilities have improved, they've been able to build boats with less material. The older boats were built much more solidly. This opinion has been repeated by many. Also, materials that were common in the 80's and 90's have become scarcer. The price of teak for instance has skyrocketed so modern boats have taken on more  of a recreational vehicle camper feel. 

Mark, captain of Tabasco which was launched in 1986, said he preferred the older boats because the hull shapes were dictated more by sailing and sea keeping performance than interior living space. Tabasco, for example, had a hull that tended to cut through waves with a sharp bow and the aft section that narrowed. Modern boats tend to have much flatter bottoms and much wider after sections so they tend to, I am told, ride up on waves which has the effect of causing a lot of unpleasant slamming when going over rough seas. When a sailboat slams it's unpleasant and always feels to me like the boat is going to come apart. 

Tabasco had a huge influence on me. I remember what immediately struck me about it was all the ways the sails could be controlled. It had more lines, winches, and stuff I didn't understand than any boat I had seen up to that point. Even the bend of the mast could be adjusted while underway. Tabasco was a proper sailors boat. Being a platform for guests was definitely secondary to it's open ocean sailing performance. 

I continued looking at boat ads. Terry and Dana had talked very highly about the Island Packet brand. These are extremely solidly built boats that if you happen to end up in really bad weather, this is the kind of boat you want. I am told they are around the world class boats and very safe. That reputation intrigued me and seemed like the kind of boat that I would want. 

So I found one for sale locally and Duncan and I set up a time to go take a look at it. It had the same electronics that Aravilla had. It had two heads. Air conditioning and a ton of other features I was looking for. 

The night before I was sitting at the bar talking to Aaron about my struggles trying to decide on what kind of boat to get. I have friends who are older and somewhat mobility challenged. I have others who suffer chronic illnesses. i talked about the Island Packet and that maybe that was the right kind of boat because it has a reputation of being very solid and ocean capable. 

Aaron, being the Zen Master of McGinty's, asked me then, "Remember, why are you buying a boat?" 

"To learn how to manage every aspect of a boat of this size, but I want something that my local friends will like but that my sailing friends will also like."

Aaron then replied, "First and foremost, this is your boat. Your friends will deal." It took me some time to get comfortable with that thought. 

It was at that moment I noticed that the very cute young woman sitting next to me had a photo of an Island Packet on her phone. This led to a conversation. It turns out her father was a lifelong sailor and was currently living on a boat in France. She had asked him his opinion of Island Packets. 

"We call them Island Buckets. They are bathtubs." was his response. This lead to more questions and a list of his favorite boats, all of which were at the top end of the market WAY out of anything I could afford. This was, however, a fortuitous conversation. 

The next day Duncan and I went to look at the Island Packet 44. It was owned by a young tech guy who had dreams of working remotely while sailing all over the place but his company had ordered everyone to return to the office so he had to sell it. We crawled all over the boat. It was certainly a 100% sailors boat. Every inch of space on that boat could be used to store something. This produced what I felt was a cramped feeling. The heads were of the problematic Vacuflush design and didn't work all that well. Tabasco had those kinds of heads and they were a source of constant problems. The engine on this boat looked beyond beat. It had a lot of leaks. But the boat seemed solid and looked like it might work. It had a very shallow draft so could go just about anywhere. The engine did have over 4000 hours of runtime on it, which was curious, I thought. 

As we walked away from that boat we came up an identical boat where the owner was outside working on it. I asked him a few questions about it and how he liked it. "On the Chesapeake, between June and September, don't even bother. This boat is so heavy it needs 15kts of wind to get moving. All you'll do is motor which is why most of these boats have so many hours on the engine." 

It was that moment that I realized an Island Packet was not the right boat. I need a boat that can move in light air. So I came to understand that a full on round the world ocean going yacht was not the right boat. I needed to find something else. 

So I started to think about features. The non-negotiable features I was looking for were:

• a boat that was first and foremost designed to be sailed for real, not a "dock queen" primarily designed to be a floating condo at the dock.
• shallow draft at most 5.5 feet. 6 feet would be too deep. 5 feet would be better
• two heads
• large enough that my mutantly tall friends would be comfortable
• air conditioning because in the summer I tend to overheat badly and I would want to use the boat as a floating office
• generator to run the air conditioning when I'm away from the dock
• something that could sail in light air
• something that was solid enough to take offshore. I called it "ocean light". Maybe I could take it to the Bahamas or further into the Caribbean.
• somewhere between 38 and 44 feet
• something that was configured in such a way that real sailors would enjoy sailing it. I was thinking about Dana and Terry.
• something where all the sail controls were routed back to the cockpit so it could be sailed without having to go to the mast
• not a plastic boat
• not a flat boat
• The boat had to be safe or able to be made safe to ABYC standards.
• solid fiberglass hull, not cored. 

The lists of nice to haves were:

• bow thruster - this is a propeller typically in a tube in the front of the boat (called the bow) that lets you move the bow left or right in tight spaces. 
• fully battened main sail - there's all this talk about "sail shape" and how sails that have these fiberglass battens in them maintain better shape and are faster 
• a swing keel - shallow keels tend to allow the boat to slide sideways more when the wind is pushing on the sails. A deeper keels offsets that and allows the boat to "point" higher in the wind, i.e. sail a closer angle to where the wind is coming from
• a "sugar scoop" stern - basically have some stairs on the back of the boat so it's easier to get onto

Then I started to think about competing requirements:

• I wanted a sailors boat. Probably a racer/cruiser which would give me more options to allow for finer control of the sails, and thus allow me to learn more
• I wanted a boat that would be comfortable enough so that I could invite non-sailors aboard and have them be comfortable and enjoy the experience
• I wanted it to be solid enough to take offshore
• I wanted it to be light enough to sail in light air

One problem on Tabasco was that in the compromise between being a serious sailing boat and entertainment platform, it was more focused on the sailing side which meant one ended up having to crawl over all kinds of equipment and lines and whatnot which made moving around the outside of the boat challenging, especially for non-sailors or those who are a bit mobility impaired.

Duncan was adamant that I try to pay attention to my inner state and select a boat that I "like".

I continued looking at boat ads and would occasionally visit marinas. From a style point of view I was irrationally drawn to Bavaria boats. I was raised culturally German after all. They are just very appealing looking boats but they were also considerably less expensive than all the other boats in the same class, which was a red flag to me. It was then that I saw a discussion in an international boat rescue group that I follow that a Bavaria 45 had been demasted in the Pacific. 

De-masted?! Wait. What? 

It was then that I learned that the mast, the pointy thing the sails hang off of, can actually be ripped off during a storm. I don't know why I didn't understand this before but once I did I started seeing more and more posts about masts coming down. 

That made an impression. I clearly don't want a mast to come down. 

I then learned that there are different kinds of ways that masts can be mounted on a boat. There's "keel stepped" where the mast is one piece and goes through a hole in the deck straight down to the keel. I went down this rabbit hole quite a ways. There are also "deck stepped" masts where the mast sits on a plate on the deck. Some "deck stepped" mast setups having what's called a "compression post" that is on the inside and provides support for the mast. Some boats, however, don't have this, and the full tension of the mast being held in place is taken up by the deck itself. 

Then there's this concept I didn't understand. The mast is held in place usually with cables. Different boats have different numbers of these cables.  The cables are either continuous, meaning they are in one piece from the deck to where they attach on the mast, or segmented. The cables are attached to what are called "chain plates" which are stainless steel plates secured on the deck and sometimes encased in fiberglass. There is tremendous force applied to these chain plates. Dana would often comment on the size of chain plates on various boats we would pass. Larger chain plates seem to be better and stronger.

The mast is usually aluminum but the cables and chain plates are stainless steel. Modern boats have added other materials. 

The cables, called the "standing rigging", are tightened to a specification. They call it "tuning a rig". The "rig" is the entire setup of the mast, the cables, etc. As you tighten the cables it pulls the mast down against whatever it is "stepped" on, whether keel or deck. It's possible to actually over tighten the cables to a point where you can start breaking the deck or even bending the entire boat. 

Another thing I leaned is that standing rigging failures are far more common than I ever imagined. These's a phenomenon called "crevice corrosion" that was not well understood even into the early 90's. Stainless steel if deprived of access to oxygen tends to lose it's electrons and rusts from the inside out in way that is completely invisible to outside observation. Island Packets, for example, had their chain plates enclosed in fiberglass and because of this process they had a tendency of breaking after a couple decades. The cables that go horizontally around the deck of a boat that hopefully prevent you from falling off, called lifelines, were often encased in a vinyl wrap and are subject to similar corrosion.

These days, some insurance companies, will actually require that all the standing rigging be replaced every 10 years. 

So I pondered that I should only consider a keel stepped mast. That seemed more solid to me. When I mentioned this to Dana he replied saying that AraVilla had deck stepped mast since it was a catamaran and that I should not just dismiss deck stepped masts. The disadvantage he said was that with a keel stepped mast that goes through the deck,, because of the forces involved, they tend to move in the hole in the deck opening it up to leaks. 

The more I learned the more challenging it became to try to make sense of all this information and then match it up to the boats available and be ready to pick a boat when one came along.

I decided, somewhat randomly, that I was going to look at boats made between 1986 and 1999. 1986 because that's when Tabasco was launched and 1999 because by then boats in the class I was looking at were getting too expensive. 

I tried to come up with a budget. Just like a motorcycle, I reasoned the acquisition price was just one part of it. There would be repair, upgrades, and equipment costs. After talking to several captains who had bought used boats who told me what went wrong and how much they had to put into them, I came up with a rough estimate that for the class of boats and age I was looking at I would end up putting 100% of the purchase price into making it right. This was just a guess based on what I had read and been told. (You, of course, know what Morgan Freeman would have said at this point.) 

I continued looking at boat ads. 

Some time ago Terry had mentioned that he was looking at a Jeanneau Sun Odyssey 54. I mentioned that I had completely dismissed Jeanneau because we had a 2016 Jeanneau for one of our sailing classes and I just didn't like it. Harking back to his comments about features versus brands, "Don't count Sun Odyssey's out. There was a time where they were bringing out higher end boats before Beneteau bought them. They were really solid nice boats." 

So I started paying attention to Sun Odysseys in earnest.

Most of the boats I was coming across that might fit the bill were either in Europe, the Caribbean, or way too expensive. I looked into maybe flying to the islands and looking at a few boats there but was strongly dissuaded. I was told many boats there are abused charter boats and by the time you go through the whole import hassle most of the price advantage would be lost. 

After looking more I came up with a "would be nice" budget and an "upper end" budget. I wondered if I could get a boat, refit it, and equip it for under $150k. My upper number was $200k. Why can I do this? I'm single. I have no wife, no ex-wife, no children, no girlfriend, no family, no debt at all, and I made what turned out to be some very good money management decisions 10 years ago. None of this was planned. There was no goal. I just ended up here and now it's possible. 

All the boats I was seeing, however, were way outside of the budget I could manage. So I started to think this wasn't going to work or might take quite a bit longer. I wasn't willing to spend an amount of money that would alter my future. There's no way I'm taking a loan for a boat.

I adopted a different tack. I decided to come up with a profile for a seller and try to buy a boat the way you buy a house that you're not in love with. (Never fall in love. It is a way to lose crazy money.) You dispassionately buy the worst maintained solid house in a good neighborhood. You know, the one that hasn't been painted, where the lawn hasn't been mowed, and maybe they went crazy with paint. But it's all surface stuff and the bones of the structure are solid. Maybe you even find a seller who can't be bothered with the process of selling. 

So I figured maybe, assuming a decent boat that I could start with, I could find a boat where:

• the seller can't be bothered with the work of selling it
• the boat looks filthy but has some indication it might be solid
• and maybe it's in some super inconvenient place but still in the US
• and probably not at a time of my choosing. When it shows up I need to be ready to move. 

I continued paying more attention to Sun Odyssey's. Thinking about what Duncan said about paying attention to any twinge of "like", I found I was really drawn to the woodwork in these boats. They are just beautiful. They have their "Deck Salon" version which has a deck with a higher ceiling. But then I came across older ones that were sleeker without the deck salon that seemed like much more serious sailing vessels and they came with optional swing keels. The woodwork in these is even nicer. I noted that unlike many modern boats they had hand rails all over the place which is key and points to it being designed as a boat to be sailed.

There was a two stateroom, two head, two shower version made.

Most of them were in Europe. There was one in British Columbia. I started reading posts about the older ones where owners who had "upgraded" to the newer versions missed how the older boats from 87 to 94 sailed. But there are so few available for sale. I continued perusing ads just biding my time.

Then I noticed one in Bucksport, South Carolina on the Intra-Coastal Waterway (a.k.a. ICW) where no sailboat should ever be. It had a generator, two cabins, two heads, two showers, two zone HVAC, a swing keel, and it was filthy but the photos of the interior had the nicest woodwork of any boat I had seen to date outside of the super high end boats. It was 44 feet long so at the extreme upper end of boats I would consider. The electronics were clearly original and completely clapped out. I dismissed it initially because I believed that it might be structurally unsound. I just couldn't wrap my head around the idea that it might be solid.

I continued looking at other boats for over a month, maybe two. 

But I kept coming back to this one boat. The asking price for it was $88k. (I just looked one up that's for sale with Seattle with an asking price of $109K but no genset or air conditioning.)

Then I paid a bit closer attention to the details of the ad. The seller had a statement in the ad, "Don't even bother contacting me if you do not have your financing in place before I show you the boat." 

"Perfect." I thought. 

Swing keel, check. 

Genset, check.

Height and length, check.

Two heads, check. 

Air conditioning, check.

Racer/cruiser configuration, check. 

The more I looked at it the more it started looking like what I had been looking for. Most sailboats have a door in the cockpit that either opens or is a set of slats that can be lifted out making it easier to get down into the salon. However, this is also a way for water to get into a boat. This isn't so much of an issue if you're just coastal sailing but offshore it can happen that a wave fills up the entire cockpit. Wayne has had this happen. In that case, the pressure of all that water can press against the door or slats and force it open flooding the salon and possibly sinking the boat if it happens often enough. Not good. This boat, on the other hand, had not door. There's just a solid fiberglass wall and there's a solidly built hatch that slides back. So you step up and over this was into a drainage well and then down into the salon. And it has these really nice hand rails around the companionway (way down into the salon).

The drains in the cockpit, called scuppers, are huge. There are what are called "Nanny cages" around the mast that you can lean against if you have to do any work at the mast. It's a safety thing that really appealed to me. And the rig, to my inexperienced eyes, seemed pretty serious. It had more cables than other boats I had looked at and also had a thick cable heading to the back of the boat (this cable is called the "back stay") which was adjustable, just like Tabasco.  Well, on Tabasco it was hydraulic and on this boat is a big screw thing, but the effect is the same. You can adjust the bend of the mast. That's just cool.

The more I looked at it the more the way the boat was configured would remind me of Tabasco. This appeared to be a sailors boat but not 100%. The cockpit looked reasonably comfortable and easy to get in and out of and the interior looked simply gorgeous. 

I read up more on these boats. The hulls are solid fiberglass reinforced with kevlar. With Kevlar? In 1991? Apparently, they are known for being very solid and have a reputation for sailing well. I came across many posts of regret where owners had sold and wished they hadn't. 

I pondered some more. No matter what boat I acquire it is going to represent a serious risk. I may buy it and get it through a survey and have the engine blow up immediately afterwards. There might be hidden structural damage. There are a whole host of problems especially on a multi-owner older boat that don't become visible until much later. But maybe this could be the right boat. I wasn't sure but I realized there was no way to be sure. Maybe going through the process, if I could structure things in such a way so I could walk for any reason, might teach me something. And then I also understood that I was potentially risking the entire purchase price only to have it be a total loss. $88k is a ton of money to potentially lose on such a frivolous silliness. But similarly equipped boats, assuming it's not totally shot, were priced around $140k elsewhere. 

Hmmm. 

I contacted the broker and said I was a cash buyer. I asked him a few questions about the boat. It had been on the market for months and was getting very little traction because of the location. It was an hour and half drive away from his location. I looked up the brokerage and was curious why they were listing this boat as all their other boats started at $250k and ranged up into the millions. "I'm doing this as a favor for one of our delivery captains who goes to my church." he explained.

Perfect. 

He said if I was interested in the boat, because I was so far away, that he would suggest he go up to the boat and do a video call with me and show me anything in the boat that I want to look at and that I could take as long as I liked. "If you're going to drive all the way down here, I want you to be confident that there won't be any surprises. I hate surprises." 

He did exactly as he said he would and went to the boat and spent well over three hours with me on the phone showing me every inch of the boat, but even so through a cellphone camera there's only so much you can see.  There were a couple items that raised questions but try as I might I could not find one show stopper. He started the diesel and it started immediately and sounded good through the phone. The same was true of the generator which it turns out is a Lugger 6k unit, which I'm told is a desirable genset. The interior looked really good. Everything looked very dry which surprised me. 

I thought about it for I forget how long. 

I asked a couple of sailors to look over the listing. "It's too big for you, Yermo. You'll never be able to handle that boat." was one of the responses I got. 

I agreed. It was too big. 44 feet is a lot of boat. But I thought I'd go through the process and see what it's like. This was the first contender and even if I decide to walk away it'll cost me some fuel, a hotel stay, and the cost of a haul out and survey, but it'll be the first time I had the opportunity to crawl over a boat in roughly the class that I was interested in and it would provide me valuable insights into when I find the "right" boat. 

The problem was the seller would need to move the boat 30 miles to the nearest marina where it could be hauled. He was not willing to do that unless he had an offer. 

So I called the broker and offered 20% under the sellers asking price with a contingency that would allow me to walk away for any reason whatsoever even if it's just I don't like the smell and will get the full deposit amount back. 

After some time, the seller reluctantly agreed.

A date was set and to my surprise Wayne offered to meet me there to offer a second set of eyes during the out of water survey. 

And so it began.