I know it's about crime, but would a "Master Criminal" have a bounty at all? I would think the master would be the one who doesn't get caught, right? The award should be called "Awful Criminal" or something along those lines, becuase I manage to escape bounty in all holds when I commit crime.
I agree with the OP. A "Master Criminal" achievement should have been calculated by keeping track of the "value" of crimes committed in each hold, regardless of if the person was caught. Having a bounty means you aren't that good; having a bounty of 1000 in each hold means you are incompetent at everything except running away.
IMO killing whole clans of reiklings, bandits, marauders, thalmor, falmer etc. etc. without anyone knowing / caring and looting their houses and bodies, thralling them, storing their bodies in your cellar etc. etc. makes you the sickest and most demented master criminal, serial mass murderer in existence.