Lots of people buy boats in Florida that are "Loop Veterans" use them to do the loop (after all, the boat already knows the way!), then sell them a year or two later. Do they get what they have into the boat out of it? Probably not, but compared to possibly renting, or leasing a boat for the loop, they WAY ahead $$ wise.
HOWEVER: Understand, that while you own the boat, any repairs are ON YOU! If your engine suddenly takes a dump and requires replacing, you are going to be into your Loop boat for a lot more $$ than you initially thought.
That being said, I think it's eminently doable.
This is exactly what THIS couple below did:
Great story, and they went an extra step of purchasing with an LLC, blogging about their experience, sold the boat after (if I remember correctly) two years and wrote off the expenses when they published the book!
Not for everyone, but it's a thought!
Our current boat, that we purchased in the PNW, took to Alaska, then down the West Coast, through the Panama Canal, and to our new to us home in Florida is not the best Loop boat. She draws 5.5', and has an airdraft of 28' . . . .
Fast forward to last month . . . . and we had a Mainship 34 follow us home . . . . The perfect loop boat.
There's a member on TF who will be listing his Mainship 34 shortly. I tried to get friends interested in it, but they're dragging their feet. I'll send him a link to this thread.
Best of luck in whatever you decide!