The best RAD cordless drill with the best "bit" that easily drives winches is the Milwaukee at 11 lb / 5 kg and 40% less expensive than the very neat Winch-Rite.
The Milwaukee will easily hoist a 250 lb/113 kg man up a 60 ft/18 m mast.
IN ADDITION it is ALSO a very powerful cordless drill . . . afloat and ashore . . . at no extra cost.