I have a 2000 380 with in-mast furling. I have found a few things that make it much easier. I haven't had to go on deck since I started using them. First, the main sail needs to be wrapped pretty tightly around the furler to prevent it from bagging out and jamming in the mast slot as it unfurls. To wrap it tight, I have one turn of the main around the cabin top winch so that I keep tension on the main as I am grinding the furling line on the other cabin top winch. I have also found that the boom uphaul needs to have the boom at a just-so angle to the mast for sail to furl evenly into the mast. You will have to play with it a bit to see where the sail furls without wrinkles. When you find that spot, then I suggest marking the uphaul line with rigging tap forward of the line lock. If you do that, you can release the uphaul while you are sailing, if you want, and still the set it to facilitate furling when you need (although I don't usually mess with the uphaul). I agree that an older main sail will be baggier and more difficult to furl; however, the things I've suggested worked pretty well even when I still had the 16-year-old main. I hope that this information helps.