The sail shouldn't hang up if you are lowering it head to wind with no load on the sail. Might want to go up the mast and carefully inspect the sail slide track to see if there is a ding or spur that is trapping the slugs. Lubricating with a dry lubricant also helps though needs to be repeated a couple of times a year to remain effective. Strong track should take care of any hang up problems if you want to spend the money.

I've run all the mainsail handling lines back to the cockpit. Reefing is double line, one each for the clew and tack. Installed 6 part two speed main sheet blocks that is convenient to the helm to control the boom. The six part tackle made trimming the main way easier. Would consider going to an 8 part to make it even easier. Have lazy jacks so dropping the main is just releasing the halyard and flaking the sail when the boat is back in the slip. Makes sailing my 35' boat a piece of cake without having to leave the cockpit except to hoist the Asym. Used Anderson 12 ST winch for the main halyard. If I did it over, would go with a bigger two speed winch. The self tailing really makes it easier to use both hands to put power into raising the sail the last few feet.

FWIW, I'm in my 7th decade so no spring chicken.