[quote=Dogboy]As said above, the two sleeves are supposed to be there. Check condition of the sail track and the mast head sheave. But keep in mind that it is not uncommon for mainsails, especially older ones, will become difficult to raise the last few feet. Later Hobie 16 mainsails have teflon in the bolt rope covering to help reduce friction. Older mainsails did not have this feature. Also if the bolt rope stitching at the head of the sail becomes frayed or worn, it will increase friction.
Other things to keep in mind- Assuming that the luff track is OK and the sheave turns freely, you want to make sure that the bolt rope and luff track are clean. I would wash both with soap and water. Then spray the entire length of the mast track using silicone spray or McLube spray. Unroll the mainsail in your yard and do the same thing along the bolt rope. Also check the batten protectors along the luff (front of the sail). If your battens are in too tight, the plastic protectors can drag along the mast and increase friction.
It is not uncommon to have to feed the mainsail into the track at the bottom and physically push it up the mast (especially on older sails). Its easiest to do this with two people (one working the halyard and the other working the sail) but it can be done solo if necessary. Pull the sail up with the halyard as far as it will go, then grab one of the batten luff protectors and push it upwards while at the same time taking care to ensure the sail feeds into the track smoothly. The bottom portion of the sail will be all wrinkled. Then pull up on the halyard and the sail should go up. Work the sail up a little at a time until it's all the way up the mast. Then engage the halyard slug into the hook.
The last thing, if you have one of those stainless steel feeders that screw into the opening at the bottom of the sail track, remove it. They cause more problems than they solve by just adding friction and another thing for the sail to get hung up on. Take it off and then reinstall the screws with a little silicone caulk so the mast doesn't leak.
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