friends who disguises insults as jokes

When they "go too far," it means you interpret it as intentional. Doesn't matter if they say they're just teasing.

Punches in the face are funny.. just sayin

killerilluminati if they do go over that line in the the sand you need to take them to one one side it was acceptable for a friend to treat this way and you did not find the comment funny but before you do just make sure you are not take what was said out of context and was a harmless comment

Does he poke fun at himself as much or more?

It depends on many things