After using CCleaner a year or two now, I just notice that it doesn't clean out the bin in outlook pro. How about having it added in (as two other email programs).
I know and have known a lot of people that don't setup the properties on the deleted bin, so the stuff sit there for years.

I'm unsure how hard that'd be. Outlook stores its data in a single, large file up until Outlook 2007. Opening that file and deleting data would likely be somewhat problematic as many folks have password protected the PST files and such.