My long distance was in the pre-container days working my way thru the university as an ordinary seaman, US merchant marine. Several ocean passages on liberty class freighters, as crew on shrimpers, and deckhand on Ms river pushers. but I know enough to know I do not know enough...
Sound like great experiences but not really qualifications. I like the last part best.
I know I'm late to the discussion but I'd agree with the ones who suggested shipping the boat. I am pretty much in agreement with John, Paul, (Betcha you thought of the Beatles) Rick and Dave.
Mother Nature isn't done beating the crap out of the East Coast. Our Michigan weather is not spring like (for sailing and spending nights on the boat in a marina with two heaters cranked up) until late May or even June, and what we get, the East Coast gets. We might get some teaser 60 or 70 degree days but we also have a lot of 30 to 40 degree nights. I've launched in May with snow coming down.
Outside of the weather that early in the season, and the way things work with yards, supplies, cure times and temps for paints and OOPs's you might consider adding the cost of hotel/motel expenses for as much as a month, while working on the boat in an unfamiliar area. It might even take a that long, dodging the weather while attempting to work on the boat. Don't forget Murphy!
A "New to ME" boat of that size, age and price should be considered a day sailer or a weekender. Not something to spend a month on and certainly not one that I'd take on a month long trek like you are planning. Maybe if I was younger and more adventuresome, I might consider it. One Nor'easter and the sea and winds are confused for as much as two or more weeks as far south as the Virgins. Made for great sailing but that was on a much larger sailboat.
That boat should be easily trailer-able behind a pick up. I trailered a previous 26' S2 behind an old tired Suburban and launched it (shoal draft). It could also be an add on with another boat heading south with a commercial carrier. Most trucked boats are heading north for the summer and the rate might be less with a trucker covering "deadhead" miles.
Whatever you decide, be safe. Let us know what you finally decided and if you went, I'd like to hear your experience.