While the sale of the boat is fresh in my memory, I wanted put a few thoughts down on my experience as a boat owner over the last four years. There’s a lot about the experience I enjoyed, and a couple things I didn’t. These notes are here to help guide me in the future if and when I decide to look at buying another boat. Perhaps, they will help someone else too.

What I really liked

• Sailing!
  Obvious, perhaps, but must be mentioned. Lots of good times on this sailboat. We won some races, and lost some quite spectacularly. We anchored out and watched fireworks. We explored Jamaica Bay. There were more champagne sails than I can count. You don’t always know beforehand when you’re going to have a truly great sail, but you can feel it when you’re out there.
• Flexibility/single handing
  With your own boat, you can do pretty much whatever you want. I spent several years at sailing clubs, which were wonderful. But, one usually needs to give up a little flexibly to have a smooth running club. Generally, you won’t be able to take a boat out at odd times or for a whole day. Single-handing is also verboten at the clubs I know.
• Making it my own
  Don’t like the way something is rigged? Change it! Don’t like how that ding in the fiberglass looks? Patch it! Setting things up your way, perhaps with some trial and error, is one of the best parts of owning anything. Learning how to do things like eye splices and soft-shackles are not only useful skills, but very satisfying. I also didn’t mind doing small maintenance or repair projects, so long as they were within, or a bit of a stretch away from my skill level.

What I didn’t like

• Hauling Out
  Hauling the boat (and putting it back in) bothered me more rather than less over the years. To the point that it became one of the reasons for selling the boat. Most people seem just fine with this activity, so I’m not sure why it caused me so much anxiety. Perhaps it was because I couldn’t do it on my own and I needed to ask for help. Next time, I’ll plan and budget for putting it at a yard and have them deal with it.
• Sanding the bottom
  Sanding is terrible, nobody likes it. Some hate it more than others. The boat came to me with many, many layers of bottom paint, much of which I sought to remove. This meant a lot of time under the boat, at weird angles, getting covered with toxic paint dust despite my efforts to contain the mess with a shop-vac. Even with help, it took me a few sessions to get reasonably smooth. Painting was a joy compared to the sanding. In the end, sanding and painting a few times taught me a valuable lesson: Pay someone else to do it. The cost was worth every penny.

One thing I didn’t mention above was the cost. While I didn’t love spending money on maintenance and operating expenses, I understand that things do cost money. Advice to my future self on costs: Set a realistic budget that you’re comfortable with, then try to stay within that budget, roughly. Don’t track every penny–spend the time and energy you’d devote to expense tracking on sailing instead.