Well the second one is just plain illegal. The first one is very possible depending on how OP handles the aftermath.

The boyfriend wanted the roommate to watch him pull a rabbit out of his hat, but his roommate kept insisting that "That trick never works."

They're*.

Always one ass hat.

There's always someone stupid, calling someone else stupid. Take note on how I used your homophone correctly.

How exactly does being stupid equate to being old? If OP had children who did this same thing, would you make them pay for it?

Because they are contractually obligated to inform the landlord- OP's boss in this case- and pay for who they pick as the contractor to do the repair since it was caused by one of the renter's. Plus, it just says "a huge hole" which means it probably isn't just a fist sized hole. My guess is that one or both of them fell through the wall, which could require that the repairperson cuts out the entire damaged section of dry wall and puts in entirely new sections, as opposed to doing something that is more of a patch job.