The question is are you genuinely interested in his well-being or just playing out an empty ritual? Personally I find it tedious when people ask me how I am when they don't really care and would probably get annoyed if I was honest. Saying hello is enough as far as I'm concerned, unless an honest answer to how are you is welcome. I'll generally reciprocate a hello even with someone I don't like and wouldn't greet first.
Number 2 though does seem a bit off. Dealt with manager like that once. Several people warned his manager that he was making the workplace unpleasant, then senior people started talking about leaving if he wasn't removed or reigned in. They eventually canned the guy after their three top technical people had jumped ship. Three more left anyway because this guy had managed to sour the whole environment around him.