Just want to get a general idea of what the common pain points are, and what the common education goals should be for our higher-ups/other departments/teammates.

I've once had a boss that requested background images in emails that both:
a) allowed replying/forwarding without the 'black reply' problem and
b) allowed the email to be printed in multiple pages from Outlook 2013.

This isn't possible, due to how Outlook 07/10/13 handles the bulletproof background's VML object; and it would only allow A consistently, since the VML object cannot print on multiple pages unless they were actually seperated per page. I tried explaining how differnet Microsoft's VML language was, even after I found an online resource on how to write to it, and how it quite simply wouldn't allow the multiple printing. The boss's response was "It's just code, you can figure it out".