I can't address your specific issues. I found that I could keep the chuck in the drill in one direction... don't recall
if it was forward or reverse. With a two speed winch reverse and normal represent two speeds. I can check this out on Shiva's set up and get back to you. But I ended up using the higher gear
(I believe)... slower speed for the winch which would not loosen the chuck.
Millie is used on the starboard forward coach roof winch under the dodger
. The D handle cannot turn as it is stopped by the dodger
bow. So I don't have to hold Millie she is supported by the winch bit. When I press the trigger, Millie tries to rotate counter clockwise around the winch... but held by dodge bow the chuck turns instead... but this seems to tighten, not loosen the chuck. If I reverse Millie the chuck loosens.
Shiva's main is 440SF and goes straight up without a hitch. I raise it bow to the eye of the wind
. I'm very happy with Millie.
life is good for several hoists. No prob really as I have plenty of time for recharge. Spare batts are spendy.