I travel alone, and use the "back up balls" for hooking up my TT. Having a power tongue jack and a drill for scissor-type stabilizers makes everything much easier. Be sure and get good extension mirrors (if yours don't extend) they are critical for switching lanes and when backing. I have a camera on the rear of TT that I use primarily for backing. Just returned from a week long trip, I used the camera on trip up, but never plugged it in coming home. It is primarily helpful when backing (I get a warning of that tree limb before I hit it).
Drive through sites are the best, and most times I am able to find one. I have found my biggest challenge is backing at home. Somehow I struggle to go in at the same angle and turn the same each time. Sometimes it is easy (yesterday was pretty simple) and sometimes I seem to struggle (on those days my neighbors will have to be patient when I block the road).