This is defintely going to be included in the V8 software. Be aware though that the operating systems will likely need to be 'similar' due to table numbering difference between ECM controller calibrations. For instance comparing an LBZ Duramax to an LS1 is probably not going to be too useful.
Your best mecanism to manage that scenario is going to be through a diligent file naming convention on your part. The reason is that the calibration obviously doesn't have any awareness of if it has been flashing or not, let along into which ECM controller.
It might be possible to introduce (although the file format for V8 may not accommodate this) the update to the .CTD file upon a completed flash of the calibration. This might simply indicate that the calibration has been flashed, and probably all of your files would inevitably be marked like that and therefore somewhat negate to purpose I think you're after.