Lawyer or no, I would be surprised to find that an HOA couldn't force an owner to re-caulk a bathroom. What's the purpose of all those damn inspections if not to discover and fix this sort of problem?
It's hard to force a lawyer to do anything. Thankfully the property manager had a personal relationship with him, and could just say, "Look, don't turn this into a big deal - just caulk the bathtub and stop the leaking already." But for that single phone call, I would be at least $15-$20K poorer.