I have no problems insulting people. Most need it, a few just ask for it.
It can be somewhat annoying, though, to insult people unintentionally. I like to save the jovial, flippant ill-will for when it’s most effective or the subject sets themselves up for it perfectly.
A warning for all: some people get really insulted if you over or underestimate their knowledge of your religion.
You should not assume people know nothing about Orthodox Judaism. Some people do know things, and get mortally insulted if you suggest that they don’t.
You should not assume that people know the basics, either. They get mortally offended when you carry on a conversation as if they know what you’re talking about when they really don’t.
In actuality, most Earthlings know what I like to call Hollywood-Orthodoxy. The know The Nanny, they know Chanukah decorations, and they know Matzah. They know the aspects of Judaism that get represented mainstream media. They know Curb Your Enthusiasm and Seinfeld.
The easiest way to avoid insulting people by accident is to first figure out which sources of popular media they are getting their information from. Then, you can act like they know the areas of Judaism represented and explain the areas that are not.
Worming this information out of people is another issue altogether.