Just wanted to provide a quick update.
On the beer that was weakened: I did not re-boil, but the yeast seems to be fine. I think I'm going to mix up a pound of extract powder in as little water as possible and try and dissolve that in it to help make up the flavor.
On the leaking worm: I grabbed another pair of the SS clamps, and tightened the two that were already on there. Did a batch yesterday, and no leaking. I was thinking about switching it out to a pair of sharkbites though. I'm also moving a faster chiller up on my wish list. Waiting for the wort to cool is taking forever now that I'm doing the full 5gal batches.
Thanks again for all the advice. I'll try and remember to post up how it tastes when it gets kegged!