Well, that's the thing...they missed during what was, truthfully, a pretty long window for a small-market team. They've been very competitive since 2013. That's 8 seasons of competitive baseball. Most small market teams' windows, if they get one, is MUCH shorter. Lets look:
TB - Have made the postseason the last 2 years, and the WS this past year. How long will it last? Who know, but history says not long. Aside from recent history, they made the playoffs 4 times in 6 seasons from 2008-13.
BAL - They've been garbage for most of the time since the mid-90s with the exception of 3 playoff berths in 5 years from 2012-16.
MIN - Were consistent playoff participants for most of the 2000s, but were regularly stomped. Are now in a run of 3 appearances in 4 years. How long that continues remains to be seen.
KC - Outside of 2014 and 2015, they've been dead since the mid-80s. They did at least get a ring.
OAK - They've made the postseason 11 times in 21 years. They typically go through cycles of 3-4 good years followed by 3-4 bad. Have not advanced to the WS since the bash brothers 30 years ago, though.
MIA - Outside of their 2 successful postseason runs, they've mostly been trash in their 28 seasons. They snuck into the postseason with a 31-29 record this year and were swept.
CIN- Made the playoffs 3 times in 4 years from 2010-13. Made it this year at 31-29 and were swept. Outside of that, they've been bad.
MIL- Have made the postseason the last 3 seasons (this past year with a 29-31 record). Outside of that, twice in 35 years.
PIT - Nice 3 year run from 2013-15, outside of that, they've been arguably the worst franchise in the sport since the early-90s.
COL - Have reached the playoffs 5 times in 28 seasons. Got to a WS in 2007 and were jailsexed. Made the playoffs in 2017-18 and are now bad again.
Really, to me, CLE, MIN & OAK are the model small market teams as far as wringing out the most sustained periods of being competitive. Others have bubbled up for short windows and went right back to long periods of being lousy. And despite 8 years of pretty damn good baseball, CLE still was perpetually in the bottom 1/4 of the league in attendance. Hard to expect the owners to spend when they don't get people to the park even when they're winning.
Shouldn't have blown it to the Cubs, because history tells us we're probably in for a 3-5 year total rebuild.