Re: difficulty raising mainsail the last few feet
One other thing I do with my main is to hoist it up as far as it goes, then use the cunningham to get full tension on the luff. I cannot tenstion from the main halyard alone to get proper tensioin, not really sure why, maybe the plastic slides get cocked and jam on the mast track. In any case, the cunningham works well and gets good tension on the lower part of the sail. Although it sounds like your sail is jamming well before you could downhaul with a cunningham to tension.