Like I don't know how one would possibly prop HBK above Flair in an objective all-time greatness contest.
Ringwork: fairly even
Mic work: significant edge to Flair
Drawing power: significant edge to Flair
Historical influence on the sport: edge to Flair
Before we even worry about HBK-Flair though, HBK's going to have to deal with Ricky Steamboat, and that quite honestly is a really difficult match for Michaels. A person could very reasonably go either way.
Ringwork: fairly even
Mic work: fairly even
Drawing power: fairly even
Historical influence on the sport: edge to Steamboat
I lean Steamboat right now, though my mind could change.