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I start in 1901 and play with fictional players, but otherwise try to re-create real-life history as closely as possible: real leagues, teams, parks, uniforms & logos, expansion and franchise movement, etc. At the start I have the American & National Leagues, the Eastern (eventual International) League, American Association, PCL, Texas League, Southern League, Negro League, and Cuban League. As the years go by I add the New York-Penn (eventual Eastern) League, Mexican League, Japanese League, etc.
I normally like to quickly sim thru the 1901-1919 seasons, then take control of the KC Monarchs when they first come into existence. I'll stick with them until the late-1940s, then make the move to MLB, choosing one of the worst teams to try to turn them around. I sim all the games, cuz I like to move reasonably quickly thru the seasons and watch the long-term history unfold, but I do it on a 1-day basis so I can check all the box scores, and a lot of times I will play out and manage my team's postseason games.
The one thing I do that's not realistic at all is that, beginning in the early 1950s when I have enough foreign leagues to field teams from 8 different countries, I start holding a World Cup tournament every 4, 5, or 6 years. Since there's (still) no option to do something like this automatically, I have to create it "by hand", moving all the players to and from their national teams. That part of it is kind of a pain (hence only doing it every 4-6 seasons), but I do enjoy going thru all the leagues and selecting each team's roster. That's always the point in the sim where I start feeling like I'm getting to know about all the players in my little baseball world, and not just the ones on my own roster...
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