This is a typical description. Matter of fact, I saw the same thing going on at the recent Hobie 16 North Americans. Some experienced sailors have this problem, but if done correctly... it can be easy.
Biggest mistake in raising a sail, on every Hobie model, is to try and hoist by just pulling on the halyard. Especially at the final 1/3 of hoisting, you have to feed the sail in from the bottom and pull only the slack you can create with the halyard. Pull too far and it wedges in the feeder and luff track.
Cat sails have lots of luff curve. The masts are straight when unloaded. There is bound to be friction between the two. As you pull harder on the halyard, the sail's luff takes it's curved shape and wedges in the luff track. To make it easy, I stand in front of the mast. After getting the sail up most of the way, I stand on the crossbar facing the mast. I hold the halyard in one hand and reach up to a batten pocket protector with the other hand (just above the feeder opening) and shove it up the track a bit. I then pull the halyard up a bit. Just repeat until hoisted, but avoid pulling harder on the halyard than there is slack in the sail.
Check out the Sail hoist and halyard lock FAQ on the Hobie Cat Forums.
http://www.hobiecat.com/community/viewtopic.php?t=371>> 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. <<