I love this question - it always comes up - how do I get into my league?
Do you follow real baseball? Do you have a favourite team? Do you follow them?
Do the same in OOTP - get to know your team, get to know your players, and get to know the league. Simming 1 year at a time I guess you get to know who wins the Cy and MVP every year, but not much else
You have to immerse yourself in it, make it your own little world.