1. A CEO unwilling to hear anything but "yes", who sees unproven technology & "creative" solutions as easy fixes (see point 1) & rules as something to be gamed, bent & warped (see point 1).
2. Personally I find the job interesting, stimulating & challenging, I work with a bunch of intelligent & interesting people, & there's minimal office politics. Unfortunately those who do like that sort of thing are often the ones who climb the greasy pole to escape controlling & participate in point 1.
Day to day you can largely ignore what management are up to & what happens at work stays at work, unless something really bad or unusual happens.
3. I'm not overly familiar with the current course but it'd only be basic stuff that was relevant, so not exactly hard to grasp or learn. Might mean an easy ride for a short time but don't bet on it.
4. Most of us work enroute so it can't be that bad! I've only worked enroute so can't personally compare but I enjoy it - the sectors I work have plenty of variety.
5. Unfortunately we work in a "sterile" environment these days & you don't get in without a valid operational reason. Take up the offer of the GA info night as you should get the opportunity to talk to an active controller who hosts them & have a tour of the ops room.