Hello, Mr. Jackson!
It sounds like you've gotten yourself into a pretty complicated email management scenario. I've got something similar set up for my plethora of email accounts as well, so I'm very familiar with the pain you're likely going through.
That being said, I think your project scope is pretty straightforward. I'd be happy to take a look at the document you've got and help provide some advice.
For background, I have been managing Google Apps domains since Apps was first launched, and it has been my go-to solution for quite some time. I started my career managing Exchange servers, and was a heavy user of Outlook for about five years.
If this sounds like a good fit, I'd love to work on this with you. Looking forward to hearing from you, either way!
Sincerely,