What are the challenges/issues with owning a boat and putting it in a slip while living a ways off (say, Tennessee, for instance), and hopping a plane every week or 2 to go sail?
This would be vs. purging everything here, moving to the water and doing it from there. I'm not sure I'm pure liveaboard material, and even if I moved to the water I would still want a place on the land. So if I can have a lower cost of living where I'm at and take advantage of ridiculous cheap ass airfare to fly down every week or two, live aboard while I'm there, learn to sail, and do some short trips, what are the costs and other issues to consider?
Depending on where you are and where your boat is cheap airfares may be non existent or if they are cheap now, some airline executive can change that with a stroke of his keyboard.
Next, most of us that own sailboats are not in the financial strata that can afford to pay someone else to keep our boat up for us. That means we do maintenance, lots of maintenance, ourselves. Traveling, at a not insignficant expense, to enjoy a long weekend on the boat might seem like a reasonable idea. Making the same trip to spend 3 days, sanding, scraping, painting, varnishing, cutless bearing replacing, ect, etc, etc, will probably rate differently on your valuation scale.
That said, I do know some folks that live at some fair distance from their boats. What I observe is they don't use them much. Even if they show up at the marina fairly often, the chores always seem to keep them at the dock, then they might get in a week long cruise each season and some short daysails.
If it were me, and I couldn't live within a mornings drive of the boat, I think I'd plan to do a long charter once a year and leave the maintenance, insurance and slip costs to others.
FWIW, after 5 years of driving only 4 hours to our boat, we've decided its too hard so we're moving the boat closer to us nearly doubling our annual slip expense, but reducing our drive by more than 1/2.