HI Sail361
This is not normal and I was experiecning a similar difficutly as explained. I think my problem was due to the battens and the covers (if you will). Last year, I spent about $100 to have them re-sewn and was still having a problem with 2006 vintage sails. The sail kept getting stuck, whether I was letting out or taking it in.
So I contacted Neil Pyride and explained this problem and another that I was having (I had some UV rot on the leading edge of the sail where it sticks out, when it is all furled up. These folks were pretty good, I explained my problem, they indicated they were hearing similiar issues from others and I sent my sail to them. They fixed both the UV rot at nocharge and added a larger pocket to cover where you insert the battens.
Of course I have not tried out the sail yet as I did this in Dec 08 (it takes about 4-5 weeks for this as they send the sail to Asia), but I am hoping their fixes covering the battens work.