First off, how large is the school? The smaller the school, the more likely it is for a conference. What type of school? Public or private?
I went to public schools that were relatively small (principals that were GOOD principals knew kids by name and got involved more than the assistant principal). And since I've already had a few go-arounds with the principal at my son's school (still waiting for her to say something to me for not signing the stupid sign-in book... *evil typical bad-guy grin*), I'd say they DO get involved. Elementary school, yes, but... you get the point. It's a small school in a rural area. PM me if you want ideas on school size and whatall...
As for trouble? Something fun that gives him a feeling of control? Well, there's the old standby of bullying. There's also theft, fights, general picking and plucking that all kids do.
There's also the argument with the teacher and being rowdy in the classroom. Think of the classclown on a more "showy" level. Saying sarcastac things during class, making jokes, making fun of the teacher, and basically creating anything but a possible learning envrionment. The kid would be getting the attention, taking over the classroom by doing so, and gaining the control he'd want. It would be fun, no one would be getting hurt, and if it's a small school -- parents would be called in for a chat.
Not sure if that helps, but maybe it's at least a starting point for ideas???