I would make sure the luff track and bolt rope are clean and lubed with McLube or spray silicone. Spray the entire track and also spray the entire bolt rope. Personally, I would have a hard time justifying investing any money in work on a 30 year old sail. If you can get it up the mast reasonably well, just deal with it and save the money to put towards a new sail in the future.
Thanks for the reply. I've tried spraying the hell out of the bolt rope with McLube and it doesn't help. There is a spot on the bolt rope that the cover has worn through and the rope is actually sticking out. I'm going to take it in and see how much the repair would be and if it isn't bad I'll just have it done.
The sail is in pretty good shape for being 30 years old. Still pretty crisp because it wasn't used a whole lot until I got bought it last year. Also I've just started sailing solo so I'm trying to make it easier to setup and go by myself. Last night I battled the main sail for 30 minutes until I finally got it up.