After doing a decent amount of reading on ADVRider (and searching craigslist) I found a 2001 Suzuki DRZ400S with just under 7500 miles on it for sale in Hagerstown. Went out last weekend, took it for a test ride, did some more research on them and liked what I saw, so I picked it up today for $2100. 
Given that my total motorcycling experience is basically this test ride and the MSF course I took a month ago, I liked it a lot. Clutch was very easy to modulate, brakes felt good for what little I know, and the extra power over a Nighthawk 250 was more than welcome . I didn't really feel uncomfortable with the seat height at a stop, but if gets to be a problem there are lowering kits... I can see where riding it at highway speeds would get old very quickly, and I can definitely see how the seat turns into butt floss after an extended period of time in the saddle, but hopefully I can find something once I get comfortable enough take longer rides.
Here it is:
Already ordered some farkles for it (rad guards, bash plate, and case guards from ThumperTalk) and bought a jacket (Olympia Patton, fits perfectly). Going looking for overpants and boots tomorrow...
