I've done a bit of road trips where we camped at night instead of staying in a motel/hotel. Usually we've focused on more nature areas and usually hiked a couple times. Good stuff. I've also done a few total roughing it trips over the course of a couple days, but that was still with some sort of vehicle for storage and with something like twenty people (geology field trip), so it wasn't that tough.
If you're thinking about buying gear, I'm generally partial to backpacking gear even though I'm not a backpacker. It tends to be more space efficient, easier to setup, and just nicer overall. Of course, that comes at a price. When does your quarter end? Will you still be camping in summer? If that's the case, you can probably skimp on things like the sleeping bag since it'll probably be warm (I don't know where Cumberland is, so that isn't necessarily the case). A good tent and a nice sleeping mat will go a long way towards making things more comfortable though.
Funny thing is right this instant I'm packing up to take a trip starting... soon, like now. My move to the East Coast will also be something like a road trip and we'll be camping along the way. Should be fun.
