These days it is hard to say whether there are better prices in Fla than on the Chesapeake. Historically the Chesapeake and Florida had very similar prices but the boats in Florida were a lot more beat up due to their tropical exposure and year round usage. One thing about the Chesapeake is that there generally seems to be more boats for sale and a wider variety of boats on the market.
I doubt the price difference on a small boat would make enough of a difference to make it worth while to buy a boat in Maryland and sail or trailer it to Florida.
I was not the person who mentioned the C&C 27 for $5K but he did mention CRAB and Spinsheet. Crab is a organization who provides access to sailing for people with physical limitations. They get a lot of boats donated and resell them moderately cheaply. The couple boats of theirs that I have looked at with people were nicely cleaned up but were not in especially good condition as you would expect out of a donated boat. Spinsheet is the local sailing magazine which features a bunch of classifieds. SpinSheet - Boats for Sale