I know, I know, most of us don't have any idea who our system administrator is or what he does. If you have a clue, you figure he's like the email guy , and more often then not you zone out after 5 minutes of conversation with him. Traditionally, they are not the most skilled socialites and their techno babble can have you going in circles.
But they are the key to getting organized online, and you cannot have a techno revolution at your school without him. So do your homework. Get on google and learn something about unix, or linux, or servers, or whatever. Better yet try to learn about the software you want to use and generally how to install it.
Then buy the guy a beer or lunch and ask him to install it for you. If you're lucky he actually will do his job, and be excited that someone from the nongeek universe actually knows what he is capable of. Then ask him about solutions to all the great projects you've been dreaming of. He may just know about a lot of this stuff, most of which is free and open-source. Geeks love challenges, takes one to know one, and if you present yourself to be marginally knowledgeable, then the computer guy may just feel that spark that gets him to work. If you can get the system administrator on board you are well on way to getting it all.