Tight
I will try to add to what has already been said with my trouble free InMast H-36.
When furling in put a rap of the outhaul line around the winch and don't point into the wind but instead go off the wind either port or starboard and you will see that the sail is being push to the side of the mast slot and helping keeping presser on the sail as it go's into the mast and keeping the sail tight so no wrinkels going in.
I do furl in my sail with out a winch just by hand but I got good at this over many years since 07 and when my boat was new yes I pointed into the wind but the sail would bang around like crazy and am sure not good thing for tthe sail.
The thing is what ever it takes for you how to do is make the sail go back into the mast tight aand no wrinkels,try letting the boom go to port side and this will help putting presser on the sail as it go' into mast.
meet with another sailor to help you,practice at the dock
Nick