Tesla is already in this situation for all of the used cars. There is a whole mishmash of features that you may or may not have from the big hitters like AP to the little things like Chill mode or hill hold.It's also difficult to explain to a new owner 'Yeah, you need the old CID althought you have MCU2 because the previous owner didn't do a full upgrade. The old CID is more epxensive because its a computer instead of a screen'.
It just adds tons of problems by doing a half baked upgrade
Regardless there is no retrofit right now. Everything is just speculation at this point. Personally I'm in the camp that Tesla won't ever offer a retrofit (regardless of what Elon tweets). If they do who knows what it will look like or how much it will cost.