Thanks crowds, I am in IL, and the trip is planned to AR. Great advice there, especially about the layovers, so I will have the wife check out spots along the route at different timed intervals and start planning the trip(Provided I can get what I am looking at). I am considering getting a second WDH for this, one with the sway control built in, and not the friction type that has to be disconnected to back up.
As far as trailering, I have been doing horse hauling, and you are right, it is nothing like the big rig stuff, but the techniques to drive are very similar, so a lot of my over the road experience does come into play, which is helpful. I see too many people out there pulling more trailer then they should, driving much faster than they should and cringe every time I see it, knowing the consequences when something goes wrong. Not Pretty. The one thing I know for certain, the TT won't be nearly as stable as the horse trailer is due to it sitting with a higher center of gravity. This is why I am opting for sway control in the hitch, even though the truck has built in sway control, its reactive, not active.