I don't see it happening since the OG xbox is right on that knife edge between old and retro. I own a couple games on steam that were released on disk for xbox: Hitman Blood Money, Flatout, Morrowind etc. The games are available on PC and modern consoles in ways stuff like classic SNES games were not until very recently. Also, no offense, but Nintendo folks are willing to buy literally the exact same game on five different consoles. Digital releases and stuff like The MCC is the Microsoft solution to those mini-consoles since Live was such a huge part of the xbox experience. No point in walking around Blood Gulch all by your lonesome, and no point in manufacturing a physical item when you can just release it digitally and drive sales on your existing platform.
IIIIIF MS did decide to release one I would like to see system-link implemented in a big way. Bring back the xbox lan party! Wireless controllers, system-link, 1080p upscaling, and a couple of the most popular MP games like Halo 2 or NFS: Underground 2.