Is this truck and trailer combo doable for this trip?

You are far better off putting most of the gear in the trailer, not in the truck. 100 lbs of gear put in the truck equals 100 lbs that goes 100% against the payload capacity of your truck. 100 lbs of gear loaded in the trailer, adds about 12 lbs to the tongue weight, which means only 12 lbs goes against the payload rating of your truck.