As someone whose first match was v Blackpool reserves in 1965 (aged 5) I was probably a bit to young to fully appreciate the management side of the whole thing but what I can tell you is that watching the 1966 cup final winning team, and yes I still remember it, then the teams through to the 69-70 Championship winning team was magical for me as a kid! To have seen the Ball, Harvey, Kendall thing at its peak was really something special! However the selling of Alan Ball to Arsenal saw it all come to an end!
The 70's with one or two exceptions, Bob Latchford and Andy Kings goal in the derby were highlights, were pretty dire!
Then the 80's and the return of Howard Kendall! Great times starting off with that back pass at Oxford! 2 League titles, God knows how many trips to Wembley, but what I would say the "football" was different, still great to watch don't get me wrong, but different! We played some great stuff but first of all imposed ourselves on the game before then going on to play the great stuff, typified by the Bayern Munich game - what a night that was!
Both great periods to be a blue, but to answer Mikey_Fitzgerald's original question I think I would on balance go with Harry Catterick, the reason why? I think the 69-70, the School of Science team would have beaten (just) the team of the mid 80's, and it was Mr C that bought HK Goodison!