He was more geeky and less super objective, rational and efficient when he made his appearances. Personally I believe the chaotic touch when WoW was younger is the main reason many people love to remember these times. I mean sure - people exploited the chaos by stacking to certain things like classes etc. to get their goals but overall for most of the players it was indeed just too chaotic to get personally accounted for everything. What then happened with "bring the player not the class" and the complete overhaul of the game systems as itemization of stats, professions, raid/dungeon difficulty etc.
I'm however not sure if Kaplan would have not ended just at the same point where we are now or worse (taken you actually prefer old wow over current) - so he has the fortunate position to represent the time "before the shift".