There certainly are some pearls of wisdom in this thread, @Lostroninn. Do you have name we can call you buy?
Anyway, Stan and Mitch summed things up pretty well. You can go from truly vintage driving experience in the traditional VW-based Speedsters to thoroughly modern cars underneath classic shapes (Beck's new chassis for Speedsters and Coupes or a 911-based IM). As long as you are educated and come into this with your eyes open (which means expect to have to tinker once in a while), you'll have one of the best automotive experiences possible. It's all about choices and budgets.
BTW, I'm in Charleston, SC and suffer the same humidity hell every summer that you do, albeit a bit shorter in duration (May-Oct). My next one will have AC. We're moving to the Smokies in a few years when I retire.