We lucked out and it worked for us
There's the same view out the windows of a $30,000 boat as a $3,000,000 boat.
Worked for us as well, same view out the windows of a $100,000 boat as a $3,000,000 boat
One piece of advice and then I will sit back and read.
NO WOODEN HULL BOATS
End of my advice.
Glad we never took your advice
If this boat has soft decks and dry rot move on.
We got some soft decks and dry rot
No biggy and reasonably easy fix
All cosmetics, not structural
Cost of repair was very well compensated for in almost give away price
If you have none of these skills then you want an estate boat that has been sitting for years unattended because the owner lost his health but not his desire.
This is how ours got cosmetically run down
The OP speaks of finding a sad looker with "good internals." My problem with this approach is that more than likely a boat with poor curb appeal will have an equally poor looking interior and poor mechanical maintenance. The "bones" as some call the hull structure might be ok, but the boat would not be something that could be "put on the road quickly."
Ours looked very sad externally, opened seams, rotten bulwarks bad enough that hawse pipes had fallen out, exterior varnish shot, covered in bird **** and dirt.
No one had enough vision to see past that
Internally she was fine, we were out of the water and back in using her inside two weeks, working on her as we live/cruise as the OP suggests he would.
Sand the shot varnish, rolled in brown paint.
4 years on and no issues that wouldn't be found on any vessel used full time over that timeframe.