I just went through this, Jared. The reason you're seeing the spike in demand in the NJ area is because of Hurricane Sandy. Do you NEED a boat now, or can you wait until the end of the season or beginning of next season? If you can wait, I'd suggest it. Life will be a lot simpler.
I bought my "new to me" 1980 31' Allmand at the end of March in Deltaville, VA, which is North of Norfolk. The boat was federally documented and registered in VA. That's the way most states handle it, USCG handles the "title" to the boat, but it must still be registered in the state if it's going to be there more than a certain number of days a year (in NJ's case, I think it was more than 180 days). I did not have to register the boat in VA; I will have to register it in NJ, which is where I inted to keep it (Barnegat Bay). NJ DMV told me that I couldn't register it until the USCG documentation had been appropriately transferred to me. That process is a LONG process (several months). Your NJ boat license should be sufficient for your short "stay" in VA.
The bigger issue will be the logistics of getting to the boat, ensuring it is in good shape, and then getting it home. A 27-28' can be trailored, but that is going to be EXPENSIVE. Otherwise, you're going to have to sail it home. Sailing it home from Norfolk, you have two options: inside, and outside. Inside involves sailing up the Chesapeake Bay, over the Chesapeake and Delaware Canal, down the Delaware River, and then out to the NJ bay of your choice (there are issues with many/most of the inlets to the bays, which we can discuss later in your planning). This is, if you're sailing only during the day, at least a 4 day drip, and may wind up being 6 days just to get to Cape May. Add on another day if you're going to keep the boat in Wildwood, Avalon, Ocean City, or other places South of Atlantic City. If you're headed north of Atlantic City, you can basically tack on at least 2 more days. The outside route is faster - probably 2 days - but you will be sailing through the night, and there are VERY few places to duck in if you have trouble or if bad weather comes up. Check out http://www.activecaptain.com
and look at the nautical charts for the two routes and you'll start to understand why I chose to move her up the Chesapeake.
The other logistic you'll have to contend with is how to get to/from the boat for the initial launch. You'll be luckier, in that in Norfolk you have an airport and, if I recall correctly, a train station. Deltaville had neither, and it was expensive to get there. So expensive, in fact, that I could afford to hire a captain to move my boat part of the way (to the Annapolis area) for not much more than it would have cost me to get down there.
In my case, the captain's trip was a blessing and a curse. He tried to move the boat in a timetable that worked for me at the time (which I appreciate) but he wound up moving her during some very strong winds. The engine was taxed, and it looks like it was pushed a little too hard. The damping plate shattered, causing the engine to lose propulsion a few miles from the intended drop-off point. I'm now looking at several thousands of dollars in repair fees to get everything working again. If the boat had been local, it probably wouldn't have been pushed so hard so soon, and I may not have had to deal with this expense for at least another year or two. On the plus side, though, the propulsion issue may well have happened while my family was aboard and we were racing to get back to the slip before a storm came in.
As to your size selection, is there a reason you aren't going a little bigger? 27-28 is a bit tight for a live-aboard, IMHO. Others here will disagree, and I can be a bit of a hoarder (though not QUITE as bad as the folks on the TV show), but 27 is small for those purposes. 30 is decent, and 32-34 is better. But have you looked into where you'd keep her?
BTW, where in South Jersey are you? I grew up in the Laurel Springs/Blackwood area just off Route 42.