just look for the worst and longest contracts... that's teh biggest factor. a team that may have won >.500 this year could be the bleakest possible. when they start their decent, that's when it's the worst.
you joke about ootp19 tigers... imo, the 2018 tigers will be easier to turn around than the 2015/2016/2017 tiger teams (in ootp). they may lose alot, but with a 7-8ish market or whatever they are, you can quickly turn it around without the draft.
they are my hometown team, so they are always a re-build to me. i can always do better
but seriously, i just handle contracts in a significantly differnet way, i can't stand any mlb team's financial situation.