Phycho,
I few thoughts.....
First, charters are not $10k. Heck, if you're very inexperienced, charter a small boat for a few hours to break the ice and get familiar....any size will do. And later charter a cabin cruiser/trawler of sorts instead of a fishing boat, unless you want to go fishing, but that's not the goal you posts.
As for your TN/KY home on the water...that's the BEST idea you've had so far, and you would absolutely want access to the Cumberland/Tennessee rivers. And in that area, I'd be surprised that you couldn't live on your boat there. Now, you have a "base" to operate from and a place to store your RV, car and junk, PLUS no marina costs which is a HUGE expense, and you have the boat close by.
Now, if you've never owned a boat before, I could argue to pick up an inexpensive ~20 ft single outboard (with a good motor), and play with it for one season. Learn rules of the road, boat handling, basics.
For a second (or first, if you're up to it) boat in that area, I could argue strongly to get a very popular boat that has some creature comforts (cabin, air, heads, cooking), like the smaller trawlers (Roseborough, Camano and others), OR a cabin cruiser with outboards. Good starter boat and can do a ton of cruising with them (including the Great Loop) and if you don't like it, or want to get bigger, not hard to sell.
I could argue strongly against an older "project" boat, unless you just like to work for free and tinker. Financially, you rarely make out and if your doing major fix up you wont have time for cruising.... and some of those older projects take years to complete, and aren't worth what you paid for it. (that's just my opinion).
As for insurance, easier to start with a smaller boat and I could argue to only get liability if you don't like the prices.
BUT, in any case, get a good captain to train you! That's a MUST. Also, regardless, learn the systems on the boat and learn how to maintain them.
Now, you haven't mentioned a wife or significant other. If so, what does she say? And if you don't have one, get one... they're fun and will give you something to complain about if the boat works fine.
Now, after a few years of boating you might figure out what boat you really want.