It sounds like your school has three too many managers. Too many chiefs, not enough Indians.
Were I the school administration, both the alums would have to go. They're not school employees, thus have no business being there. They're a liability since they're not likely covered by any insurance policy, and in some areas, it is illegal to be on a school campus unless you are a student, employee, or have some other official business being there. The administrators may overlook it, but there is probably a policy in place forbidding it. It may seem like the alums are a Godsend helping out the tech program, but in reality, they are holding it back more than anything. They will have to leave sometime, and until they do, the
current students can't mature and take ownership the way that they need to. Schools need that fresh start, even if it is rough for a year or two after one of the "head tech's" leaves. The best way to avoid this is to begin training students very early on so they will be ready for more responsibility as an upperclassman. They graduate, and the sophomores and juniors take their place. Rinse and repeat. Alums really shouldn't be allowed back except on an extremely irregular basis; perhaps to student teach a tech class or give a presentation on college tech and what to expect.
Asst. Mgr #1 is risking a lot if he really did give a set of keys to Asst. Mgr #2. Now, they are both in the wrong, and possibly breaking the law. If one of them so much as loses a set of keys along the way, even that can open up a huge can of worms. I guess that same type of liability comes back on you too, so please be careful. Any under no circumstances should you ever take the keys home with you. That is possession of school-owned property and I don't think you'd want to get caught with that on your shoulders. Especially if the place gets broken in to one night, or something goes missing.