sounds like you have planned one hell of a road trip. Ambitious? Yes. Impossible? No. My family drove from washington, DC to Alaska way back in '95, sold the car and flew home. some 8000 miles in 30 days packed in a 'yota minivan. some called us crazy but we did it.
Its too bad you wont be stopping in New Orleans on this trip to pick me up!

im trying to figure out if i can make it to Sebring this year. it falls almost perfectly in my spring break, but i might not get the cash to get rental car there, and the greyhound bus doesnt seem to be a great option... none of my friends are crazy enough to want to spend their spring break at the 12 hours of sebring.

maybe ill hitch-hike.