When I got mine, I could not feed the brass stopper through the sheave because when the previous owner installed the mast bob, he put two bolts through the mast head, slightly above the sheave. The bolts were stopping the stopper from going through.
We could not figure it out until we dropped the mast to check. I keep the mast up all the time except for winter storage.
It might help to attach a small rope to the halyard shackle, and hoist the halyard by itself with no sail so you can see if it's fetching up anywhere. You can use the rope to bring it back down.
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Marc...
1978 Hobie 16 Keoke, sail# 36 84
