1. look for simple fix first ... sounds like your main halyard sheave is frozen at top of mast ... hammer taps and WD 40 ... see if it is groved badly from prior use of wire. 2. sheave at bottom of mast also will freeze ... if it is turning at all just oil. also see if grooved. 3. the main can be heavy ... mine are over 40 lbs. 4. most crews do a jump and sweat at the mast to raise sail 5. pain in ass to winch. 6. I am using 10mm for halyards ... max size but doesn't jam. See how a 9 and 12 yo handle sail raise in this video.
