If you have the budget for lessons, perhaps drive down to FL and take a week long, liveaboard fast track cruising sailing course. I think Off Shore Sailing School does them in Tampa area. I'm sure there are others. On one hand, if you do that now, you would have a better sense of whether this will be as good as you hope. On the other hand, if you don't get to sailing soon thereafter, you'll lose all the training (i.e. learn fast, lose fast).
You mentioned being in debt for life. Does the boat purchase budget include financing the boat? If so, be careful. The boat can quickly be worth less than you owe, unless you have a significant down payment. Many (possibly most) marine lenders do not finance liveaboard boats, perhaps because the wear and tear is greater and value declines too fast. I'm not sure their logic is always good, but offer it for your research. Some will say one should never finance a boat. I don't always feel that way, especially if it's your home. Although, be sober about how it may work out.
The final component of financial planning should recognize that some great percentage of cruisers and liveaboards eventually move back ashore, unless they die unexpectedly.
I'm only offering thoughts for planning. I hope it becomes everything you dream it to be. Good luck.
What you are saying is all true, and is good advice, and yes, it is probably axiomatic, that most sailers eventually come back to land to die, but until then, I want to live on the ocean
- for the first time in my life - while I am still capable of doing so.
Why? Because I was raised, and lived, near the sea most of my life, and it was only unforeseen circumstances, coupled with well-intentioned, yet bad advice, that prevented me from buying a live aboard sailboat years ago. So, I have decided that it is time to redeem that huge mistake, and [finally] eliminate that deep, lifelong regret
FYI: I plan to take a basic keelboat course at a local lake based marina in Spring 2017, and after that, want to wangle some delivery, or race crew opportunities in the Gulf, and along the eastern seaboard. At least those are my hopes anyway.
Once again, I very much appreciate your feedback, and look forward to more in the future.
Oh, almost forgot, I plan to use the profits from the sale of my house to buy the boat outright
. Unless of course, I can find a decent paying job again, in which case, I'll use that income to buy the boat, then rent out my place as soon as I move aboard. On the other hand, I just might sell my house anyway (-still thinking that one thru).