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Well there's "what would have really happened" and "just trying to make it plausible." If you wanted to get teams into the South sooner, sometime around 1886 would make sense, I think. Travel would be hard, but not impossible (though I'd recommend not trying to model travel time in OOTP--way too much fiddling) and while cities might be too small, if you were trying to do a different sort of "major" leagues, it could work.
For the West Coast, though--I dunno, I'd be hard pressed to feel realistic about going coast-to-coast until after WWI at the very earliest. It's why I'm thinking of starting a league in 1946--so I can be all over country without much issue.
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