See, even you're a bit confused by MSDN -- You're not even supposed to use the MSDN license for your own everyday use is what I've been told. So if you have outlook for email and you're using an MSDN license, that's not correctly licensed. MSDN is ONLY for development. Also it's one MSDN license per developer apparently.

And no because you still get nailed -- it's not like your reseller is the one being audited, it's you.

You're supposed to get CALs for printers accessing MS servers.

Don't ever use an MS server for DHCP, every single client needs a CAL. How am I supposed to even predict that if we allow personal devices on the guest network?

It's beyond frustrating - and the products are great, they just make it impossible to actually ever be in compliance and you need to spend an insane amount of time just handling licenses. It's really the reason I avoid MS as much as possible, and I really love their dev tools (Visual Studio is beyond awesome, I love C#.net) its just too much hassle.