Re: Truck delivery
I bought a boat in Seabrook, TX 2 years ago and had to get it back to New Orleans. I got quotes for a delivery captain recommended by the broker I was working with in Texas, and for trucking via the UShip site. (If you use Uship, definitely let the quotes sit a few days, because people will bid against each other.) The cost was about the same for the actual trucking or water delivery. But by the time I figured in getting the mast pulled, loading and unloading, it was easier and cheaper to have her delivered via the ICW.
Jimgo expressed concern about possible problems arising during a delivery with an unfamiliar boat. But presumably you had the boat surveyed before you bought it, which should have found the major issues. For the minor stuff, the delivery can be like an extended shakedown cruise where someone else will find the things you needed to get fixed anyway. Unless you are more experienced than the delivery captain you hire, he or she will probably be able to deal with whatever comes up at least as well as you would if it came up later, after the boat arrives. And after the delivery, the boat definitely wouldn't be "unproven" anymore.
That was my experience, anyway. Like they say - your mileage may vary.