Maybe this is something that is widely known and used but just in case it’s not…a very knowledgeable chap at our boatyard has just told me to splice my rode about a foot from the end of the chain. This way the loose bit can be fed easily on to the gypsy without having to manually pull the slack up.
We also have a Quick windlass and have chain and then octoplait.
We find the windlass is able to pull the chain and the octoplait but the join does not go smoothly round and into the locker, indeed it has twice bent the plastic lever which stops the chain jumping off the drum. So the method now is to use the windlass to bring the octoplait in almost to the join - though often this is quicker and easier by hand as there is little tension until the chain gets off the bottom. Then an extra pull of a couple of feet by hand and quickly push the join through the hole into the locker and wrap the chain around the drum to then continue using the windlass.
I also have a Quick windlass, originally with 30m of 8mm chain. Earlier in the year, heading for the Med and having read Peter Smith's Webpage on Anchors and Anchoring I added 40m of 14mm Polyester 3 strand. I had the same problem with the windlass that you describe. The rope was retrieved by the windlass ( the gypsy has serrated grooves which nicely gripped the rope) but the rope jammed in the plastic stripper arm. My solution was to loop a plastic tie wrap, about 5mm wide, around the gypsy and through the hole the rope/chain drops into the locker. This works a treat, no more jams.
