I guess this is a major problem area for all TheMightyHobie18 owners; I went through the same trial/error on raising the TheMightyHobie18. I now have very little problems in doing either, and here's what I did:

1) a twist shackle on the ring.
2) I now use a quick pin in the top shackle. I make sure the knot from the bolt rope is facing to the port side. I make sure the quick pin button side faces the port side.
3) Once a year, I use McLube or some dry silicone on the sails. When I drop the mast for either racing or storage, I always rinse out the spiders, etc. Once a year I spray that track, too.
4) I take my time in raising the sail; make sure it never binds in the track. Make sure your mast rotator limiter is completely loose to allow the mast to swivel a little bit.
5) When it really won't click in, moving it to starboard, then to port seems to work everytime; I can't explain it either.
5) Lowering; have someone move it to starboard while take the pressure of the ring off the hook if it gets stuck. But normally, I can just put a little pressure on it, then it will drop.
6) For doing either, make sure your boat is pointed either into the wind, or just off by a few degrees.

Good Luck,
Wyatt