Something is wrong with your phone or the OBi. For some reason the first * key press is not being recognised. Possibly that it is not limited to the * but applies to the first key you press after taking the phone off-hook. That would account for failure to successfully dial calls. Test that by repeating the first digit.
I know you said you already tried another phone but please try again. Do not use any components of the first phone. Batteries, cords, base station if cordless, etc.