To me there are levels. If I said all Red Sox fans were drunken louts, that would cross the same line Philadelphia fan stereotypes do (which is not to say there isn't some truth in both cases, based on a small fraction of people). But if I said I find most Yankees fans to be arrogant and entitled, that's a little less inflammatory, and I think the Boston fan base transformed into one that was more like New York than Chicago (and not just because of baseball, they have won a championship in all four major sports. Which also means they can just laugh it all off. Philly fans can't do that either).
The classic Cubs stereotype is lovable losers whose fans are happy to just hang out in the Wrigley and not win. That stereotype is probably going down. But I am still gonna find that more charming than another major market high-dollar juggernaut, and a repeat of the saturation "breaking the curse" coverage we already lived through recently. Under the same front office, too.
But I'll still root for them over the Nats or the AL. Love the manager, like most of the players (if they lose a series because Chapman gives up a home run I'd be ok with that too).
