I have fielded teams with no chance of winning a bunch of times. I don't play players out of position, promote my best prospects to the majors, or sign anything better than the dregs of FA on one-year contracts. My worst 6 seasons (with those requirements), in wins: 64, 64, 60, 50, 61, 59.
So it is possible to win less than 60. But each of those teams was a playoff contender 2-3 years later. So maybe it should be something like "if you win under 120 combined in 2 consecutive years, you must win 155 or make the playoffs in the next 2."