To (very) hesitantly - nervously and not certain - guess or calculate the cost, size, value, etc. of something.
"I ehhr hestimate it was something like - I don't know - twenty? Thousand? Or ten thousand years ago."
Permission of the misses, - your wife or girlfriend.
Are you joining us for a drink? Yes, but first let me get permisses.
So annoying you want to tear out your hair; infuriating; make someone extremely irritated or annoyed.
The CNN journalist found Mr Trump's unwillingness to answer his question crazifying.