Nice post. I really like your tactical reasoning.
I've dabbled a bit with a 4-4-2 diamond myself (inspired by the ROI in the Euros) but I probably haven't put as much thought into it as you.
The team I am using also has no decent wingers, but has a few exceptional CMs. The problem I found was that, defensively I was leaving too much space on the wings. My midfielders would not close down opposition wingers quickly enough and it lead to many the dreaded cross landing in my box from deep.
I dropped my experiment pretty quickly after a couple of games as I had other tactics that were working. But I'm curious as to how your team works defensively? Do you have this problem defending wide attacks and do you use any instructions to deal with it?
Thanks