Do you have a topping lift?
No topping lift.
That being said, you may have slack in it merely because it is old and stretched.
That's my thought. As far as I can tell, it's the original sail for the boat (from '76).
If that's the case, then you'll want to replace it, but how soon you do so is up to you. In many cases, you'll see performance issues with blown out sails, but the boat will still move along OK. She won't point as high, and you'll have trouble getting an optimal sail shape, but as long as you're OK with this, you should be OK for a while.
Good to know. Based on my research, replacing the sails will probably cost almost as much as I paid for the boat. I'm not sure how I feel about that yet. On one hand, it might improve my experience, but on the other hand, it's more money that I'll never get out of it when I sell and trade up.
As to the leak, a cup or two doesn't sound like much water. It may be coming up through the centerboard trunk, and "merely" splashing out the top and into the cockpit. To look for leaks, dry the boat out, then drop her back in the water, but tie her off somewhere. You could try getting some of the blue chalk that they use for "chalk lines" and making some light lines across the boat at regular intervals. That should help you find the source of the leak. But I'd check a few common stress areas, such as around the CB trunk and along the transom (especially near the gudgeons). It's also possible that the drain plug has an obstruction (debris) that allows it to slowly leak.
I may not be fully understanding the chalkline part. Is it just to see which end (or side) starts to sit lower as she takes on water? Or is there more to it?
Also, to clarify - the water isn't leaking into the cockpit, but rather, the empty(?) space in between the hull and the deck (not sure of the proper term for it).
Also, thanks for "gudgeons." I hadn't heard that term before