Matt, I think this is a super cool idea (and have been wondering since version 13 when Password Requirements were added why this hasn't been a standard feature in SmarterMail). Wherever there is ENTER PASSWORD/CONFIRM PASSWORD there should be a [GENERATE RANDOM/SECURE PASSWORD] button that will autofill those fields with a Password that meets the Mail Server's Password Requirements.
It seems like everyday I have customers who have to reset their password only to be confused because they can't come up with a secure/complex password on their own and don't understand why the screen just refreshes every time they hit the [SAVE] button because their password of "pa55word" didn't meet the Password Requirements.
Just about every Web App that has a PASSWORD/CONFIRM PASSWORD field has some kind of random secure password generator as standard issue. I'm really surprised this has been an after-thought for SmarterTools.