Hey, Brak. It doesn't at all sound unreasonable that SOMEone would do it, but I have to wonder what it would cost you to have it hauled over the road, if you called some transport companies and said "Look, anytime in April, I can give you four or six weeks and you just let me know when you are coming." that gives them the chance to fill a deadhead (empty run) and can result in a 30-50% discount off the rack rate.
On the water...Let's say $150/day for ten days, because you know eight is possible but "**** happens". And since it is the ICW...groundings happen.
You won't get a pro, so your insurance may protest the commercial nature of the delivery. But who wants to drive a bus in the ICW for eight days nonstop? If it was a sailing trip in open water, you might find four friends who'd jump at the chance, and have good enough credentials to keep you happy. (Although I'm still not sure your insurer would be.)
Might be worth calling the truckers, and taking the opportunity to do the bottom while she's out of the water.