I'll just say that, yes, the new CD-Media will handle the amount/frequency of Who-Am-I pictures. You'll also be able to easily set your current picture back to older ones. That's a ways off, still.
For fun, I threw this together just now on my lunch. It's how often you've posted a who-am-i picture from your join date to today. This doesn't count the 150some I imported from our old gallery (pre-vBulletin) .. otherwise I'd be up there with 150+ pictures .. and I've only had about 5.
Also, this isn't meant to point any fingers .. if someone was motivated enough, they could figure this stuff out .. I just have a little easier access to it. If it were serious enough, there would already be controls to prevent higher frequency & amounts of Who-AM-I pictures.
With that said:
http://www.chiefdelphi.com/forums/whoami.php
Woo.