Not a problem with the main
I've never had a problem or need to keep tension on the outhaul when furling the main, she just rolls up very nicely. I do keep tension on the genny lines though. I want that as tight as possible as I've seen some ugly results from high winds when they're left loose. As far as using the winch is concerned, as I said it's usually a case of being out in good wind. I can furl, unfurl by hand in light wind but I generally don't bother to set sail in those conditions as I won't get much speed out of her. When I sail I like to sail as fast I can. With some exceptions, ghosting along at 3-4 kts doesn't do anything for me. Actually anything less than full speed, usually the 7kt+ range, is left for lazy days.