Several things to try.
1. Inspect the top sheave. Look for cracks, etc. The older they are the more likely it's damaged or on it's way to being damaged.
2. Inspect, clean and lubricate the track itself. You want to make sure it isn't kinked or dented in a way that would narrow the passage of the rope bolt. When I first got mine I pressure washed it, pushed a wadded up piece of towel through the entire length with a screw driver (you'll be amazed at the amount of gunk you will get out), and then lubricated it with a spray like Sailkote dry lubricant or similar (which is awesome for other parts of the boat, too, difficult shackles, swivel cam cleats, travel cars, etc.).
3. Inspect the rope bolt on the sail and look for any wear or miss-alignment, and lube it thoroughly with Sailkote.
Here are some instructions I copied off the forum once:
HOIST TECHNIQUE
Keep the batten tension to a minimum. Hoist the sail slowly, while feeding into the mast opening. When the sail gets about 3/4's of the way up, begin aggressively feeding at the bottom opening and reduce the amount of halyard effort. If the halyard is pulled tight when the sail is not being fed into and up the track, you will have problems. The sail luff will pull taunt and the curve shape will bind in the (straight) mast track. Lower the sail slightly and begin feeding again.
The best way to feed the sail is to stand in front of the mast and reach around either side to "sandwich" the sail between two hands (above the feeder opening) and push the sail up the track. Pull with the halyard, only the slack created, then feed again. If the sail binds, lower slightly and begin feeding again. This technique can be done by one person, but is certainly easier with two working together. It is VERY important that the person on the halyard only pulls the slack up the mast and does not get ahead of the feeder.
Locking the Hobie 14/16 halyard:
Once the sail is fully hoisted (be sure that the sail is fully inserted into the feeder). Pull the halyard forward of the mast by 3-4 feet. Hold the halyard on the centerline of the mast. Pull hard and hold the tension while bringing the halyard into the mast. Release the halyard tension and see that the sail remains fully hoisted. This seats a small bead, in the halyard, under a two finger prong "hook" and the top of the mast. If the sail slips down when downhaul tension is added, repeat the final hoist technique again. Be sure the bead is clear to pass the hook before pulling tension on the halyard.
Good luck!
_________________ '81 H16
If it ain't a blowin', I ain't a goin'
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