I seldom have any trouble raising the sail. There is a small bracket just below the slot which guides the sail into the slot. It was standard on my boat in '85 but an option before then. If you have reef point on your sail then it is '85 or older. With the comptip mast they did away with the reef point so the halyard wire could be short. I did have a problem where I couldn't raise the last foot or so when the main sheet was too tight. With the 5 to 1 blocks, the sheet would loosen as I raised the sail and there was no problem. I switched to a 6 to 1 block. The first time I raised the sail I had the problem you described and found that I had to pull some of the sheet to loosen the boom and get the sail all the way up.

Howard