I'm glad you're enjoying Skyline. To your points:
Skyline can do this already. If you have a replicate loaded, Skyline should show you (in the Document Grid) the calculated CCS for any given transition with a 1/K0 value, based on the calibration implemented by the vendor (typically encoded in the raw file itself, but in a manner unknown to Skyline).
If you run a standard through Skyline (that is, not a lot of co-elution going on) without any ion mobility filtering enabled, Skyline can build an ion mobility library from observation of the IM peaks in the data. You could then compare those results to past measurements.
It's important to understand that Skyline really depends on the instrument for calibration - when given both a CCS and a mobility value, Skyline always uses the CCS value and relies on the vendor DLL to provide a mobility value from that. CCS is considered ground truth, independent of instrument, so perhaps we already have what you're looking for. Though, of course, CCS itself is actually dependent on machine conditions (gas type and pressure, etc) so that only gets you so far.
I hope this helps,