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The top left section of the Manager's Office screen, Notes & Tasks, is a good place to start as it'll tell you of stuff you should be doing asap. And when the top menu buttons have little red rectangles in them you should probably check them for stuff that is new.
Other than that, it's a pretty open-ended game. I think most of us probably fall into habits of doing a set list of things that we do every day, week, month, whatever. Personally, I like playing God and interjecting here or there, but mostly I'll just watch things unfold. When I played in online leagues, however, after every sim (usually weekly) I'd have a list of things that I'd do every time (checking the waiver wire, the DL, FA, the trade block, etc) and another list of things I'd do at only certain times of the year (protecting for the rule 5, etc).
Yeah, it can be intimidating starting any video game that is wide open like OOTP is, but don't put too much pressure on yourself to do things perfect. Just putter around until you find something you like, focus on that part of the game, and in time you'll find yourself exploring other aspects of it as well.
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For Beta/Devs: Full screen (1920x1080)
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