Many of the teams you're discussing here may have problems due to being unable to draw fans because of their poor performance. The Chicago Cubs have no such issues...the ballpark is always full and team promo items fly off the shelves, no matter how crappy the team is in any given year. Hence, they really have no motivation to produce a 'winner'
I pretty much quit being a fan of any baseball back in the 80's after all the stupid strikes
And I feel that players and team owners were equally culpable
....all the $$$$$ has made them lose touch with reality.