We do let the trailer down the driveway with the winch -- that is the easy part. And Cal, we do not stand near the cable when winching -- there is a remote control for the winch, and the control has a long wire. We also drape heavy carpet scraps over the cable when winching, to slow down the whiplash if it breaks.
Also, our driveway is not very steep or very long -- if the cable were to break, the trailer would slowly roll to the street and stop. But just to be safe, we wait till there is no traffic before we start winching.
It is true that the winch rotates toward the strain point, since it is on a chain. But it is so moveable, paradoxically, that there is not enough resistance to cause the cable to spool onto the drum in an orderly way -- it just piles up, unless I push the cable sideways with a piece of pipe. I have not tried using a gloved hand to do that, but I suppose I could try.
I think that an anchored winch pointed right at the trailer is the solution, as others have explained above. And after pondering the possibilities, probably a pivoting pulley between the winch and the trailer will be the easiest method of achieving that goal.
