Today I Learned

Enable Mac Keyboard Number Pad in iTerm

If you Mac keyboard's number pad is not working in iTerm, then follow the steps outlined here: http://superuser.com/a/565179/175226

Looks like the answer is to go into Preferences->Profiles->Keys
and load preset of: xterm with numeric keypad.

You will lose any default key mappings that you already set in your iTerm profile already, so you may want to do this in a brand new profile so you can bring over your old mappings to the new profile and not outright lose them like I just did.