I did start working on implementing this. We would love to hear your feedback about how exactly this should work.
You can install a special build of Skyline-daily here:
This special build of Skyline-daily is currently newer than any official Skyline-daily which has been released. The documents that it saves will not be compatible with older Skyline's or Skyline-daily's, but you can always use the "File > Share" menu item to save the document in an older format that would be compatible with older Skylines.
This special build of Skyline adds a "Peptide Spectrum Match Count" column to the "Peptide Result" section in the Document Grid.
You can see some screenshots showing what that looks like here:
Let us know if this feature is what you are looking for and whether there is any disconnect between how it works and how you were either hoping or expecting it would work.