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I'd recommend you start with the 2012 season or a historical year that appeals to you. In the startup process you can turn off minor leagues if you don't want to contend with them. They'll also take care of themselves without you needing to interfere, so it's your choice.
Choose your team, go into the team screens for pitching rotation and depth charts, and let the manager or bench coach determine those.
Take a look at the player ratings. I think the game defaults to ratings of 1-20 which makes them pretty easy to understand.
Get your season started. Try managing a few games - actually playing every at-bat, or possibly every inning. Try simming the better part of the season: that is, let the program simulate the games, and you see the results.
You'll see the season develop like a regular season and, just like following your favorite real team, you will want to get in there and make decisions to bench players, play others more.
As you get through a season or two like this you will naturally discover more and more features of the game and learn which aspects interest you. You can choose to micromanage and pore over every front office and on-the-field detail, or sit back and enjoy the show. You can go in and tweak the settings in an attempt to create more realism/fun/victory - whatever you're after.
Fortunately OOTP is a game you can progress into. If there's a level of detail you are not ready for, you can skip it for later - or forever, if you like.
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