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For your first league, you've got to go fictional. A small league, as Peregrine suggests, will be much more manageable, and easier to experiment with. Plus, it eliminates the possibility of, say, the Red Sox and Yankees both falling into last place, or Justin Verlander becoming a washed-up AAA pitcher. I've seen far too many posts about how OOTP "isn't realistic" because real-life players don't match their real-life performances. Don't fall into that trap; play fictional first and learn how the development engine and Talent Change Randomness work.
I would also suggest using preset financials by importing whatever year you want. Don't mess with custom finances until you're comfortable with the game - they can be a pain in the rear end to get working properly.
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