A friend's father used to put in the logging roads with a D9 tractor and would pull his 20' trailer in behind the tractor as he made his way. Beat the trailer up pretty good but he always got it in and always got it out. Lots of pull with the D9.
I would get a trailer that you don't mind beating the heck out of and so any damage is not a big worry. The shorter the trailer the less leveraged stress there will be between the tongue and the axles and this will help as well as make tighter turns possible some of the time.
Appreciate though that you are trying to put a square peg in a round hole and for this it is the "get a bigger hammer" approach that is needed.