One problem that seems to appear with historical leagues is the breakdown in accurate minor league teams. (Fair enough... it's already a pretty big chunk of database, and that's really a minor thing.)
Either way, beginning 1995, I meandered through some job offers, looked over some rosters (Cool to see the Big Unit in an M's uniform)... I ended up going for an offer in the Houston Astros organization, managing their Spring-A level club in Corpus Christi. The Corpus Christi Resistance.
Hard to buy a 21 year-old manager, but hell... it's my Baseball Universe, I can be a prodigy if I want.
I sim until the week before opening day because... basically it's almost impossible to tell what you'll have to work with as a minor league manager too far in the future. Build your rotation around some pitchers? They get called up. Bush League Ball is all about 'work with what you got'.
And that's painful at times, because if you really want to be detailed, you can spend an hour setting up your depth chart. Nevermind the strategy options. There are separate strategy sliders for 1-3, 4-6, 7-8, 9-e innings, and for +5 to -5 scores. Yes, you set a separate strategy for, say, 5th inning, up by 2.
At the moment, Corpus Christi seems to suck a bit...