Most Efficient Anti-Jamming Mainsail Hoist

I wonder what is the most efficient way to feed the mainsail boltrope into the mast track where you have fewest jams and can do it fast. First will it feed better with mainsail on the port or starboard side of boom? With the right hand doing the winch cranking, how best can the left hand be used. Is there some foolproof aid/gear piece that will keep the luff edge from sometimes jamming in the track entrance. Maybe someway to just use your thumb as a pressure guide. I would like a easy simple way so that when I have newbies onboard they can do it successfully with minimal instruction. Looking for something that will make it simple like when a mainsail has luff slugs already in the track. The metal halyards in a winch does it make it nice so that you don't have all the rope mess in a pile needing to be coiled and hung-up.

I frequently take newbies out on my boat. This is a procedure that works well for me. I have the main draped into the port side of the cockpit. I attach the halyard shackle to the head of the sail from my position on the starboard side of the boom. I feed the bolt rope into the mast then show one of my guests how to feed the boltrope into the mast to guide it in. I do the cranking from my position on the starboard side. That way I can "feel" the halyard as it raises the sail. If there is a jam, I know it first and do not risk forcing it.