OK hopefully I can explain this as I see it in my head. Think cab over camper. Attach (high enough to clear the sides of trailer) permanent steel tubes of appropriate size, to front (as loaded on trailer) and back. These tubes should be heavy enough to allow other strong steel tubes to be inserted into them. The inserts will have Camper jacks attached on the other end.
Insert these into the tubing, lock the inserts in with a pin, and jack the shack up. Back the trailer up under it and lower the jacks.
The jacks can be kept outboard as far as you need them to be, just make sure the steel tubing, insert and outside, are strong enough to handle the leverage. Once lowered the jacks can be removed and stored inside (like when home) to keep out of the weather, and brought out and re-attached when needed. No winch needed. Probably costa hundred bucks for the steel plus the jacks.