I'm not sure how we're going to work out logistics, but we were thinking of buying a boat online in the keys... sight unseen. This is a big risk, but we were thinking of having local forum members maybe help us scope out the ship beforehand. It would save us the drive/flight and thereby a LOT of money.
That's a BIG RISK! But possible. Yes have someone scope it out for you, and (this is a must), part of the purchase contract should include "contingent on satisfactory survey and seatrial". Once you have it scoped out for you and you decide to make an offer, you get a list of good surveyors here on Sailnet and you hire one to survey the boat. A survey by a qualified surveyor is a must and also required if you want to insure the boat - another must.
A survey will run you, in the neighborhood of $15-25 per foot, depending on the experience and expertise of the surveyor plus the cost of a haul out, maybe a couple hundred more. Again, this is a must if you value your lives.