I'm a more than a little confused by your story... but let me add a couple of things based on personal experience. I just bought a boat, and it's a ten-minute bicycle ride away. The reason I bring this little fact up is because I have it on good evidence that this helps keep catastrophic damage to a minimum. I can and do check on her often. Don't know where you live relative to your boat, but there you go...
One more point about "sucking it up." You'll have to this time, but I'm convinced that this sailing/cruising thing can be done very very inexpensively. You aren't going to be nearly as comfortable while doing it, but being physically uncomfortable and at ease in your head -- simultaneously -- is what it's all about.
I agree with Mr. Hog. As stated above, I have no car; however, I do have a bike and various trailers able to carry all manner of boat gear such as sailbags, fenders, cradle pads, even whisker poles if lashed right and tipped with a red rag... So when I *don't* have the trailer on, it's actually a pleasure to cycle 15 minutes or so down to the club to double-check chafe gear, redeploy fenders and make sure I haven't left something on deck that could leave in a blow. I do this because I'm at a finger end and because I nearly chafed through a bowline once: if the boat had gone, it would have piled into a line of another club's boats on the beam after a 100 metre sprint. So now I check. Proximity to my house is the main reason I picked the club.
The second point is also valid. After initial expenses to achieve a pleasant and safe life on the hook is established, you can stash a 200-DVD library of movie classics, carry around 100 sailing books and 100 tradeable paperbacks, learn to become a better cook, learn marlinespike seamanship and make nautical crafts, sew sails or fish from the taff rail. You can row to and from other people's boats and get free liquor for oil changes or simple things that older and perhaps arthritic sailors can't manage easily anymore. You can go exploring out of the tourist zones. Very little of this sort of life is expensive, and it certainly needn't be monotonous.