he saw the unemployment line flash before his eyes at the thought XD the horrible, horrible things they would do with that key, that he would be blamed for
Master keys are serious business. One of those goes missing, you potentially have to re-key hundreds of locks to keep your property secure. I worked in housing maintenance for a big university, and they treated those masters as if they actually went to the U.S. Nuclear Football and not some college student's dorm room or apartment.
"Did someone escape through a window?" "Yea." "Nice." Wow. Just imagine the kind of stuff that must go on daily for that to be such a nonchalant conversation.
We can potentially assume two other things from that exchanged. One, that trying to escape out of one of those windows is so common that he could guess that based on how everyone was standing around. Two, that no one else has successfully done it before. Which makes sense if those office trailers are elevated like it seems from the exterior shot.