The difficulty is investing time and energy starting with 30+ ST games, 162 regular season then the WC success, the ALDS success , and have the chance for the WS and go down softly with a lot of your shortcomings exposed by an acknowledged better team. Overachieving is wonderful but as Durocher said, second place is first loser.
They did make the Final Four which is better than 26 other worse outcomes.