Am I hearing correctly though that NC is a bit trickier than some of the other areas mentioned? Mostly we had started thinking up that way due to the number of boats that were available in NC.
I don't think that NC is more trickier than Florida. NC, SC and Georgia have excellent protected cruising areas. The areas are less "tropical" and picturesque, more rural, however there are still people leaving from a sea, and, in some aspects, the coast between Georgia and Virginia is more "authentic", sort of.
Also there are plenty of anchorages and protected bays. You will need shallow draft boat to explore ICWW. It shouldn't be a problem with boats under 30 ft. NC town of Oriental is sort of sailing capital of the coast. There are thousands of boats sitting, some for sale, and town itself is worth a visit. Also boat storage is much cheaper there. So I'd not skip NC.
Also I don't see why you want to keep your boat on hard. There is no other reason than bottom job, to pull the boat out. Accumulating coast of hauling out will be higher than difference in wet and dry storage costs, if any, in my opinion.
I kept my boat some 3000 miles south from my place for a while. I and my girlfriend have had wonderful spontaneous three-four day vocations in midst of a winter, just fly in, get on a boat and go sailing for couple days and fly out.
After sailing Catalina 27 for a week, I, personally, don't think that this boat is all that great, I found it uncomfortable and poorly designed on outside, anything on a deck was out of sync, and in a way. It is very good boat inside at dock or anchor
I'd suggest to look at Pearson 28 (not a Triton, next version), You can find one at $10000-15000 range and this boat can take you out of sight of land when you outgrow protected waters, or smaller Tartans.
I can also pitch for Freedom line of boats, however I understand that it is sort of unconventional boats and may not be everyones cap of tea. They tend to be more expensive too.