Raise the main
First thought is that you need to clean the track in the mast. Second is to check the sail slides and make sure none of them are badly worn, broken etc. Other than that, you might check all the rollers in the system, look for bad bearings, broken sheaves. And be sure to check and make sure none of them are too small for the halyard and pinching it. Can't think of anything else. I am sure that there is a problem. Raising the main shouldn't be that difficult. On my 37, I only use the winch for the last few feet, and to tighten.