Just purchased this 2002 Getaway, bought some new sails, and I'm unable to raise the mainsail. It always gets stuck in the transition between the plastic luff track and this aluminum piece.
Here's where it gets stuck, as shown with me raising the mainsail on land:

That aluminum piece slides. As the mainsail comes up, the luff catches the aluminum piece and pushes it up. It won't go into the track on its own.
The gap you see is ~ 0.5". Since the aluminum piece slides, the gap is either as shown, or at the top of the mast.
Now, on land, I can manually feed the luff through the track and get it to the top:

I'm wondering if past owners have done something odd. The gap seems wrong. Also, I'm not sure what this aluminum piece is from. Current model comptips appear to just have a plastic luff track w/out the aluminum piece.
Does anyone recognize this problem, perhaps from older boats?
Thanks!