Assuming you don't want to exceed the ratings, you are basically going to have to strip everything out of the truck and go to the bathroom before pulling out to stay under the limits on the 1000lb hitch weight trailer. Are you really going to be able to resist putting anything in the bed of the truck when heading out?
Realistically by the time you get up above the mid 20' range, moving up to a 3/4ton for the bigger brakes and heavier suspension starts making a lot of sense...not that I would predict death and destruction if you manage to stay in the ratings.