CmBarnes-
I've bought two boats out-of-state (Florida & Texas) and hauled them both home to Boston. Both boats were in good to excellent condition but here are my recommendations for you.
Make sure you hire a good surveyor (Brian Stetler in Jupiter is VERY GOOD....
www.amarinesurveyor.com) to look over the boat before you fly down. Ask him to take digital photos and include them with his report. Have him check the stringers, transom, floor, gas tank, wiring, engine, electronics, trim/tilt, and throttle/shift cables. Some surveyors only do engine compression tests, some do more extensive engine inspections or have a deal with a marine mechanic who will do it for them.
Also, be sure the surveyor water tests the boat, and everything is in working condition. Make sure he documents whatever is not working or needs replacing and use this as a bargaining tool with the seller. After the survey, I negotiated the seller down $2k by phone/email to cover some things that needed to be repaired. I would recommend that you have a pretty firm price agreed upon before you get down there...you dont want any surprises. If the boat is a total lemon when you arrive or it just doesnt seem right, you DO NOT have to buy it. You can always get on the next flight home or just spend a day or two looking at other boats in the area.
Once you're convinced that you want the boat. Fly or drive down, (make a UHaul reservation if you need one to haul the boat home...talk to me before you do this...I talked them down from $1000 to $387) and then go check out the boat. I would insist on water testing the boat yourself too...1) to see if rides the way you think it should 2) to see if you notice anything the surveyor missed.
Also, be sure to make sure that the trailer is in good working condition (bearings, tires, lights, etc) and your BOAT US Trailer Road Service has not expired. When you get down there go the local Wal-MArt and pick up a couple of sets of bearings & seals, an extra hub, a grease gun, a jack, lugwrench, etc.
All I can say is be prepared...and then prepare some more.