I've owned two sailboats. The first one was a 30 footer that I used on occasional weekends. It became annoying because every time I wanted to use it, I had to spend just as much time fixing it. I had that boat for a decade. It was fun when I was using it and really stressful other times when I was trying to figure out how to make repairs in really inconvenient locations on a 40 year old boat. Looking back, I should have either rented each time I wanted to go out, or I should have joined a partnership with 3 or 4 other people and split the costs of the boat and split the sailing time.
The second boat was a 36 footer that my wife and I lived on while sailing full time in the caribbean. It needed just as much repairs, but since we literally used the boat constantly, the use:repair ratio was tons better. Repairs still were difficult and required physical contortions sometimes to fix and maintain stuff, but since we were sailing full time, it wasnt a big deal, since I wasnt trying to squeeze maintenance in on weekends among all my other responsibilities and desired leisure activities.
I've been back "on land" and boatless for 3 years now. I think I'm going to find a good partnership to join. A few hundred bucks a month should get 5 days a month to sail something in the 30 foot range. I dont think I'll ever own another boat by myself unless we decide to quit our jobs and sail full time again.
My advice: spend a summer renting boats. Force yourself to pony up the cash to go as often as you want to. At the end of the summer, total up the costs. Compare the money you spent to the money and time it would cost you to own a boat. Should be clear at the end of the summer if you go out often enough to justify buying.
It also sounds like you want something that will be on a trailer. Factor in wear and tear on a towing vehicle, cost of the towing vehicle (if you dont already have that), time spent on maintenance (assign your time a dollar value), storage costs (if you dont have extra garage space for the boat), additional maintenance costs if you have to store it outside, insurance on the boat, trailer maintenance costs, and obviously the cost of the boat itself (calculate it as a depreciating asset).
It definitely makes sense to own a boat in some circumstances, but most boat owners are really just paying for the idea of owning a boat, it generally would be cheaper and more convenient to rent in most cases.