I purchased my boat brand new and the bolt rope was to short. When I contact Sol Cat about it they told me to either send the sail back to be repaired, or cut the threads that attached the rope at the clew, and allow the sail to stretch past the end of the rope, Since I didn't want to wait weeks to send the sail back, and didn't like the second option I took it to a sail maker. Somehow they attached an extension to the existing rope. If the sail is in good shape, I would take it to a local sail maker to get their opinion.

As far as feeding the sail into the slot, I had that also. I folded my sail, and didn't roll it up. Placed it closed to the mast and with one hand pulled the halyard, and the other fed it into the slot. Don't think a new sail will cure that.

Now for the Halyard. DON'T use line. Replace the cable and put a swage fitting on it to catch the "hook" on the forward side of the mast, top. There are a couple of reasons why you want to hook the halyard at the top. First, line stretches, so you will never be able to get the down haul adjusted correctly. When strong winds/gusts hit the sail, the line will stretch, altering the sail shape, and not in a good way.

The second reason is by using line, and pulling the halyard tight and tying it off at the cleat, it will bow the mast to one side, (think of a bow and arrow).

You have a performance boat, but the performance can be stripped out of it if not setup correctly.

Charlie