How about instead of real-time, it's called an Edit Mode. You can go to the CSI Learn screen and get an overview of the current mapping, and if you want to make a change you can enter Edit mode, audition the change even, and then Save it. Probably the same thing you're imagining and just a semantic difference. The idea being there's only one way to edit things on the Learn screen, and you have to engage it and save the changes.
Thinking ahead, I feel like the flow of the Learn Mode UI should be left to right. You select the page you want to view or make edits on the left, then pick the device from a list, then select from a list of all available widgets for that device, and ultimately, the action you want to assign to that widget on the right (with the ability to lookup Reaper actions). Maybe, if modifiers are mapped in the .mst, you show them along with the widget. So if I have a shift button, the widget section will show the widget, and the Shift+Widget, but not show Alt or Ctrl because I don't have those particular modifiers mapped. This way, users can't make invalid selections (e.g. "why doesn't Alt+Button work, I'm holding the Alt key on my keyboard while I press the button").
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