1) I'm writing a paper for the Jr Admin as a proposal, at best id probably just be assisting because the Jr administrator is somewhat of a friend.
2) its not irrelevant because although Statefull packet inspection would stop the problem I'm not certain that it logs it. But I suppose it wouldn't need to be logged if it was being stopped.
4) The school already has a strict policy against streaming media unless it has been authorized by School Director. Hence why I believe it wold be useful to track who is breaking these rules because they are interested in suspending internet usage from certain few rule breakers.
As for the information on setting up a linux firewall an an intermediary, it sounds like a good idea that I will look into
ps. My school banned searches involving "baseball" lol.