Half the time he has no fucking idea about the rules, he's attempted to punish me in the past for instances that aren't even rulebreaks. He also defends gangsters from police as citizens, shop owners etc, in order to attempt to rip suits on a regular basis.

Defending people as a citizen or shop owner has never been a rulebreak and never will.
This doesn't state you can't commit criminal acts, such as printing. It's just stating you can't set your job to be something like "Private Hitman" or something similar.