OP here -- I have learned a lot already! For one thing, the broomstick trick sounds like a winner, rather than letting the cable end up where it wants to. Since DW is the winch operator, I like the idea of a long stick better than the idea of her using her gloved hand to guide the wire.
And the idea of a pulley is great! The winch itself is essentially chained to a wall -- the cable would run through the pulley and out to the trailer. I could easily sink a threaded socket into the concrete of the driveway and then thread a bolt through the eye of a pulley. That way, the cable could go straight to the winch from the pulley.
But keep those ideas coming -- I am hoping for a fresh start with a new (and better) winch. My ex-winch has about a quarter of an inch gap between the plate at the end of the drum and the sideplate of the the winch itself -- just enough room to jam in a couple of turns of cable. My next winch will not have that gap, you can be sure.
