Hi Aaron and welcome to the forum.
It sounds like the boat is still under warranty. You may wish to establish yourself with a local dealer who can work with you in correcting any hull leak issues. Perhaps someone on the forum from your area may have a recommendation. In the meantime, you can melt a little plastic in the hole or plug it with calking or glue to temporarily solve your problem.
Do you know if your Adventure came with the standard rudder or the larger sailing rudder? The larger rudder presents a challenge for the Twist & Stow mechanism and a little hand assist is not uncommon. In either case, there are a couple of things you can do:
1. Some silicon spray periodically in the rotating mechanism helps keep the friction down.
2. Wiggling the rudder with the directional control while lifting it helps get it going.
3. Your boat may have a loop bungee on the lifting side of the cables. Hobie has recommended changing that for a loop cable. There may be a free kit available for that.
4. It's possible, but not likely that your rudder can be adjusted too tight or too loose. It should not bind as you rotate it by hand, but not be sloppy either. If your dealer is familiar with the system, he should be able to troubleshoot it for you.