Casters or skids on back of TM?

My wife and I are making the plunge from wilderness canoeing (primarily Boundary Waters) to a TT. I am 67 and she is a cancer patient (in remission) and sleeping on the ground for days at the time (often in cold and wet) is becoming a challenge. I have a 2002 Tundra AC, TRD, 4x4. It is the sharpest p/u in these parts and I want something that I can pull with it. Started looking at Hi-Los but am now convinced that Trailmanor is for me. Lots of good info. from this site. I do have a question that I have not seen here yet. The transition from the street up my driveway is pretty steep. Is there an option to put caster wheels or skid pads on the back of a TM to take care of some limited dragging as I start up the driveway?

BTW, I've about determined that the 3124 is the one for us. Thanks for any help you veterans can offer.

Bill