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Put an electric winch on the front of trailer and pull the shack on with that and use the atv to pull it off.., Welcome to the site..
Using a winch on ATV even w a pulley could be tough since (especially in an icy parking lot) atv could slide forward when winching instead of shack going up the ramp.
I've been waiting for the metal shop in town to restock the tubular steel I need to weld up a removable frame for a winch I can mount to the front of my truck box. it wouldn't take much to run the power from the light assembly or the trailer light socket. That way I could use it for loading things too heavy to push up the ramp & into the bed & remove it when needed.
Jon, you may want to consider running a heavy gauge wire directly to the battery as a power source, I think you would be disappointed with the results of trying to run your winch off of standard light wiring. You can install a separate plug and socket to make it convenient to connect/disconnect.
Agreed, you'll fry the tail light wiring before you even get tension on the winch cable...