I think much depends on where you want to sail and what your budget
is. I prefer the Bahamas
to anything in the U.S., so one thing I'd consider is boats coming out of charter
in the Caribbean
, and keep it there, not paying any U.S. tax. Many of the boats that I've seen coming out of charter
are in much better shape than many for sale
in the U.S. that have been neglected.
One disadvantage to buying
in the Caribbean is the cost of doing the boat search, including any motel costs. Also, if you want to make upgrades, it may be less convenient and more costly.
On the other hand, if I'm looking for a cheaper fixer upper, I'd be much more likely to buy something here in the states, so I can drive my own car around as I look at boats, and also have the convenience of my car and many less expensive marine
stores available as I do my own projects.