small truck and small trailer?
A S-10 should have no problem pulling a single place trailer!
One ski up on the wheel well, the other on the floor of the bed. I used to carry my 156 Mountain max around in my Tacoma before I sold it (the truck), no issues.
I saw this past winter a guy with S-10 that he built a plywood deck just above wheels and had sled on top of wheels. also had little door at back to hold gear under the deck.
That thing is hanging out quite a bit!build a deck use 2x4s with plywood on top should be high enough to sit flat that way. use to haul a 07 phazer to lando 5 or 6 times a year that way in a explorer sportrak. tried it with my renegade but stuck out to much for my comfort.