Here's my latest progress on the winch in place pulley setup. I opted for 10lb test 0.12mm diameter PE fishing line (orange color) as the output that will interface into the first pair of downgearing pulleys of my archimedes pulley downgearing system.

This turn in place pulley achieves 2.77:1 downgearing ratio now. The motor shaft reels in 32 inches of string that is 6lb test 0.08mm pe fishing line (black) and after the downgearing pulley, the final amount of orange fishing line reeled in is 11.55". That's a much more manageable amount of runout for the archimedes pulley system to deal with to keep it more compact.

The archimedes pulley downgearing system will add an additional 16:1 downgearing to this which brings me to a total of 44:1 downgearing. The motor itself pulls at .5lb pulling force so after 44x that increases to 22lb of pulling power. After mechanical disadvantage is factored in, I estimate the finger can curl 5.5lb ideally which is about the same strength as my finger. So that's perfect and VERY strong IMO.