I'm going to question my boss about literally everything he says.
Why do you think it's necessary to question your boss?
I've seen him do lots of mistakes. He treats others rudely.
I'd say it's smarter to just question your boss on the things that matter.  If you bug him about every little thing, he might not listen to your complaints when it's a real serious issue!
I think this will be fun.
You are going to be very annoying and that will make things worse for you at work. You should just do your job and question things that should be talked about.