Originally Posted by DRFerron
The hardest part I've found is completely lowering the main underway and folding it down on top of the mast.
Center the main. Heading into the wind helps so that the main flutters and the tension is released. Have the helmsman put the boat in neutral or if you must go forward, go as slowly as possible. The helmsman should keep a lookout and alert whoever is lowering the main to any approaching wakes so he or she isn't knocked off balance and if the boat has to turn into a large wake (which means the wind will fill in the sail). When going on deck, don't forget the sail ties. If just reefing the sail this will be when you tie the reefing lines (if equipped) rather than take it all the way down. Some boats are equipped with a hook that attaches to the leading edge of the sail to keep it in position while you tie the lines.
It's easier to reef the main before raising it completely. If you know that the wind is strong before leaving the mooring/anchorage/dock, tie the reefing lines before you leave.
I've never had much luck folding the sail against the mast and have taken the easier route of just letting gravity put it on the boom instead.
Back to Ninefingers. There are many monohull sailboats in the Virgin Islands area that have have furling mains. The ones with conventional mains pretty much all have sailbags and lazyjacks on the boom. Many you don't have to even leave the cockpit to raise or lower the main. Either way it's not hard to do after seeing it done once. As Drferron says, just make sure you are into the wind, especially with full battens and lazyjacks.