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Since you specifically mentioned the 1997 Orioles team as one you've been interested in, I would start with that team if I was you.
Otherwise, just doing a playthrough on a 2016 season's team would be a good starting point as well. It doesn't even necessarily have to be a MLB team. You could do a Minor League, Independent League, or even a foreign league team. Maybe pick a team you don't necessarily have a rooting interest for or against, and see what you can do with it?
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