Nick... Yer gonna have to find your own place, really! I mean, looking through some of the stuff here, I disagree with a lot of folks (I dislike Houston, I like Lexington, KY somewhat, I think Columbus is about as boring a place as I've been to...).
F'rinstance, I could tell ya how great Madison is. We've got lakes, we've got a thriving GA community, a full 1/4th of the population is college students, etc... I love it, but you may well hate it.
I've traveled the US a LOT, and not only as a driver. I'd say that some of the places I've thought would be really good places to live were the Raleigh/Durham area in NC, and Portland, OR. You might also like Spokane, WA. A lot of other places come to mind as places I've liked but didn't necessarily want to live there.
I think your best option is... a ROAD TRIP!!!
Put your stuff in storage, throw the essentials in your pickup (don't forget Piper), and hit the road. Head west to SoCal, work your way up the coast to Seattle, head east on I-90 to Billings and then I-94 to MSP, come down this way and visit me, head over to IA to see Tony, take I-35 south to Texas (be sure to detour down US 71 and go see Diana and Chip), visit the fine folks in Dallas and then Houston, head up toward Steve, work your way over to AL and up I-65, take 94 again up into Michigan, 75 back down to 90, work your way up towards the northeast, and then take I-95 south to Florida. By then you'll have seen a lotta places and have a good idea where you want to go. Take your time, the more you're stopped the better idea you'll have about all these different places.
Oh, and take lots of pictures.