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.