Welcome to the club. Your adventurous attitude has all the hallmarks of a long future as a sailor.
Brynn wrote:
Why is launching off a beach easier? Because I can just pick the boat up and turn it into the wind while I rig it?
Yep. Also there's rarely other boats around putting pressure on you to get moving (except other cats), and you won't run into docks and other boats because of wind shifts. Also, compared to just about every other boat except maybe a steam boat, cats aren't as maneuverable while at the same time fast and unwilling to point into the wind as quickly as a monohull. Beach launching is much less stressful.
Brynn wrote:
I will double check all the batten ties for next time, I was just sure I had set something up wrong since the jib was catching every time.
It is suggested to cut the jib battens short. So short that they don't stick out past the sail, then drill a hole for the batten tie. Or short enough that just the end caps stick out. It has also been suggested to pass the halyards around a shroud to keep them out of the way of the jib, but I've not tried it yet. Sometimes, especially in light wind, when a jib batten is hung up on a halyard you'll just have to get up and grab the jib's leech and the halyard it's hooked onto and pull the two apart.
Brynn wrote:
Yes, I have an all metal mast. So the second stopper is for reefing and does not belong inside the luff track.
Right. The second stopper (meaning the one furthest from the main sail) shouldn't be a concern, but the age of the halyard should be. Consider getting a new one. At least inspect the one you have.
Also, you mentioned the halyard cleat breaking. Yep, drill out the old rivet and pop a new one on. I hope you're not using the cleat the secure the sail because it's not designed for that.