Greetings! I've been reading this forum for quite some time, but this is my first post.
Regarding the Cubs, even if we beat them in the playoffs -- hopefully we will if we have to play them -- and then lose to, say, the Dodgers, Cubs fans would probably say (in snarky fashion): "Hey, 2016! When was the last time the Brewers won the World Series?"
Still, if we're going to lose in the playoffs, yes, I'd rather it be to a team other than the Cubs.