I use a dry silicone lubricant on both my headsail foil and my main bolt rope slot which I find helps. I usually just apply lubricant to the bolt rope as it feeds in and let the sail run it up the foil/slot. I also apply the same lubricant to all sheaves and blocks as well. This is a habit which I picked up from folks I crewed with for 12 years. The previous boat has never had to clean either track after monthly lubrication cycles, so I figure there is not appreciable build-up.
With two folks aboard it is best to have one person bumping the halyard at the mast. This makes a big difference and tends to get the sails up relatively hassle free. Watch out for the bolt rope pinching as it feeds.
