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Difficult from 1871-1900, because OOTP has trouble with folding franchises. Because of this the default start for these years already has all 16 AL and NL teams. You could either accept that, or you'd need to manually make the changes until 1901.
From 1901 and up it's easy. I forget the exact terminology at the moment, but there's an option under 'historical' to have the league automatically expand as time passes. It'll take care of such things as rising finances, the switch to free agency in '76, new divisions and playoff structures and so forth.
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