Try a smaller halyard.
John: We had this problem on our H'31. The main was extremely difficult to raise. I was using 1/2" Sta-set X. I decided to drop down to 7/16" Sta-set and it made all the different in the world. It is going to cost you about $125 to find out if this will take care of the problem but may be worth it. Just some other ideas. Have you tried pulling the sail out of the boom by hand? Does it appear that the friction in cause by the boom or the halyard. If the boom is causing the problem you may want to strip it down and totally clean and lube it. You will also want to check the track to be sure that it is clean and lube it with McLube (dry lubricant). Also check all of the sheaves and make sure that they turn easily without any load on them too.
