Scott- I would agree on a “show in a vacuum” way that 2000 blows away any year in terms of workrate/cards/matches etc. That being said the most fascinating time period to watch, I think, would be ppvs from I would say post mania 12 to the end of 97. The evolutions of Shawn, Bret and Austin were all fascinating to watch and the whole evolution of the company in general.
That period was TERRIBLE on PPV, man. WCW was blowing them away with their midcard. 2000 had Cactus Jack returning, the Radicalz debuting, Chris Jericho's World title challenge, the Rock at his peak, Kurt Angle becoming a superstar, and Rikishi and Too Cool. It was, as the kids say, dope.