"Yacht" is perhaps too strong a word for what I'm talking about here.
The word "yacht" conjures up images of Trumpian three hundred footers. You know, a heli-pad and a twenty foot Donzi runabout as a tender.
No, I'm talking about affordable stuff in the 25 - 50 foot range.
First thing you have to consider, is that the pool of 25 to 50 foot boats is way heavy on the sell side. Lots of folks selling this stuff; not too many buying.
That's for a lot of reasons, but the main reason is that America's middle class has evaporated. I'll let Hill and Donny sort that business out, but the point is, the boat market that used to be the pervue of the "middle class" is gone like a fart in a hurricane...
If you're selling a forty foot cruiser that's thirty years old with a pair of carbureted big blocks, you don't have a boat for sale, you've got a dumpster issue.
Here's my advice. Pick up one of these aging beauties for next to nothing. Play bon vivant at the marina all summer. It'll run anywhere from five hundred to two thousand dollars to fuel up your aging '80's Formula or Sea Ray, so you're gonna have to keep those 50 mph blasts down the lake to a minimum, but by god they're a lot of fun. Spend your winters making up fake invoices for all the imaginary work you've done on your "classic" and keep her insured to the max.
Then, when you get into serious repair territory with the inevitable out-drive or engine problems that will cost multiple times what you paid in the first place, pull the plug. Preferably somewhere where the water's deep enough that the insurance company's investigators aren't going to insist on a salvage operation.
Good luck, and happy boating!
See you on the lake!