60 isn't alot to make the playoffs. I would make the following exception ; All playoff teams must reach the min - period. If you have a team make the playoffs and your second team fails to reach the min, as long as your 2nd team played the most live games in it's division your 1st team is eligible.
So Owner X's 1st team - goes 94-68 and wins the NL Central with 72 live games
Owner X's 2nd team - goes 86-76 and would have won the AL WC but owner X only played 52 games (most in that division)
team 1 is eligible, team 2 is ineligible.
that sound reasonable?