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Since you can get a loose car to go to the top without problem, I would be looking at the remaining cars to see if there is something funky.
Another thought that occurs to me, though is this. I assume you tied a line to that loose car so you could retrieve it from the top of the mast? Did you try holding tension on it to simulate the weight of the sail as you were hoisting it? I was thinking that if you had someone pull against you as you hoist the car, and if you find the spot where it is jamming, you might be able to take both the halyard and the retrieving line and saw back and forth a bit to see if you can feel the nature of the obstruction.
And maybe you'd find that the mast head sheave needs serious lubrication. Does the halyard lead internally back to the deck? Is it possible there's a hang up where the halyard emerges from the mast near the heel?
Just ideas.
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