I just gotta jump into this. As somebody who spent a lot of his life doing exactly what Hemi Joel wants to do and enjoying the hell out of it and having many fond memories of those trips I say do it. We are all different. Some are exhausted after 200 miles on the road and others can do 500 easily and maybe a couple hundred more just for the heck of it.
Your route will most likely be determined by the weather pending on the day you pull out. It may require some zigzagging or you may be able to just head straight west on the route of your choice. But if it were me I'd stay way south.