I have 2 elec winches mounted on my trailers - both around $200.
5.3m tinnie. One gets hauled off the beach on to the trailer - so has to lift up and on to the trailer. The other, depending on the tide has to haul my boat up a steep slope on to the trailer - steeper than any boat ramp I have seen. The first one, I have had for about 6 yrs now. No issues. The 2nd one I just fitted this yr. It did fail - turns out one end of the drive bit turns in a bush and the high load chewed the bush out. I fitted a couple of cheap bearings in place of the bush. Working fine.
I am surprised the drills are strong enough - but given the right gearing and grunty drill, it is obviously do-able. There is an advantage , as stated - with the drill in that if it fails you still have the manual winch. However the 2nd boat which I haul up a steep slope was an absolute pig at times - I couldn't do it in a single go. Too steep, too old. This $200 winch does it. And the remote function on both winches is worth its weight in gold. I have wired them to the vehicle battery - simple plug in job when the trailer couples. For $200, I would not be without them.
I pulled the 2nd one apart when it failed, looking for the cause. It is strongly constructed. The gears are taking a big load and no issue. Just a bush chewed out. The gear end has a solid bearing. The small bearings I used to replace the bush seem to be working fine.
Alan