The hat you wear matters a lot, you don't apply for a job as a Penetration tester with a black hat on.

How many people on devRant are skilled with pentesting / Offensive Security? How long did it take you to understand it? How do you keep yourself from crossing over white hat territory into grey hat territory?

Let's play a game.
Theme: Security awareness - grey-hat style.

How to play:
Post the name of the site followed by actual bad-password restrictions of well-known companies in the comments.

If no-one beats me to it, I plan to share some of the more alarming ones(or all) on a twitter and tag the relative companies as well as various security enthusiasts.