Owen, I don't know how long it's been since you've been in the states, but if you have lived in the islands for 16 years you are going to have a bad case of culture shock when you get here.
I've sailed with a friend several times and have been to Puerto Rico, D.R., seen a lot of the Bahamas, and from the Tortugas to Charleston S.C. on the east coast.
Slips in Fla are expensive no matter where you go and if you get one on the Atlantic side it will be on the ICW. There is little maintenance going on with it since 9-11 as the funds got shifted to homeland security. If you have 8' draft, be careful.
Anything below Daytona Beach =$$$$$.
Daytona to Jacksonville =$$$.
Charleston,S.C. is nice but gets cool in winter. Most liveaboards head for the Keys in late Nov. after hurricane season winds down. But you won't like the 'brown' water.
I don't care much for the Gulf side but never sailed there (was supposed to do a trip from Lake Ponchetrain to Key West but couldn't make it).
I agree that the Daytona/ Cape Canavaral area would be the most likely for the MBA job. You can get work at any Marina. :-)
Are you planning a crossing soon? Won't be long till the cat starts swishing her tail.
Sorry I couldn't be more specific.
Fishbonz