Our boat is sold now but discovered a couple years before selling her a good method of raising the main. After determining what tack I'd be on I'd stow what was to be the leeward jacks. Heading out I'd hold steady with the wind holding the sail snug against the remaining jack line side. I had the main halyard lead to the cockpit to an electric winch with a button at the helm and could look through the bimini window as I raised it. I'd load the winch and while at the helm slowly head the boat into the wind. As I raised the main from the helm (with the button) I'd turn the boat as necessary to allow it to raise under control without catching. It worked great keeping the main under control with only one side of jacks. After we were sailing I'd go to the mast and stow the windward jacks.

With the button at the helm for the electric winch and a window in the bimini raising the main was like clockwork with only 1 person and a really heavy main.

Loved my multi purpose electric winch and wish I started that practice years earlier.