I just got done putting a bunch of cherry green keyswitches into my 7bit layout plate (Which is almost identical to your anykey mod idea, but without a tenkey.
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I would say one part of designing something is all about tradeoffs. For example, you can probably have a printed OLED circuit made up that would go between the barrels of a buckling spring keyboard (though it'd be expensive). You'd have a rather large total resolution of pixels to drive, so maybe running linux or the like on a decent ARM core or FPGA (also expensive) would be what you need.
I must admit, my weak point is that sort of hardware <-> software low-level connection/drivers stuff, so I can't really help you with that.
Still, I've studied on display technologies, and there's a lot you can do with them. One reason to use OLED's is so that you can bend it to sit flat on the curved barrel plate.
Another option is to find round displays the right diameter. That might also work.
Either way, it'd be VERY expensive to test, try, and make. I would estimate easily 2X or 3X the final cost to get parts in prototypes/building/testing/breaking, before you have a "complete" project. Even still, it'd be expensive.
But that's what GH and DIY are all about! Draining your money away until there's none left.