I agree with you that the Diablo is a very well engineered piece. I dont know in what way Gryphon built their board, where or what was optimized for the dac board in general nor their usb implementation in particular. With that said, I cant imagine that the usb to spdif handoff is revolutionary, more likely it was optimized. Therefore, and this is a WAG, the usb to spdif handoff as well as the clocking is more than likely very, very good but its unlikely the clocking is a world beater. The Grimm or the better Aurenders via AES will likely make a material difference.
One of the advantages of a high end company like Gryphon designing their own dac (or phono) board is they can build it to their standards based on the optimal traits to complement the Diablo. No interconnects needed, perfect integration, etc, etc. They dont have to overbuild it, they just build it to a high enough standard and thats where they should logically stop. Its a tremendous value but thats from a long ago, multi day audtition. If you like your Diablo and dont plan on moving up the Gryphon foodchain, you are set. If you are content, then dont overbuy on the server/streamer front.We all get caught up with bringing a howitzer to a pillow fight bu the analogy absolutely applies to hifi.
In your case, assuming you are happy with your Diablo and you just want to enhance/maximize what you have, I believe that the less you ask a dac board to do (even a dac board developed by an exceptional manufacturer like Gryphon) the better off you will be. The aes input will be an upgrade from companies the likes of Aurender, Grimm, Antipodes, et al.