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I usually start with the Cubs because that's my favorite team, and I play real world, current season, I like to play game by game, and as the season progresses, I'll start to sim parts of the game. Once the team I'm simming is 5 games out of the WC I'll typically sim 1/2 inning at a time until I've simmed 5 innings, 6 games out, 6 innings, 7 games out, 7 innings and so forth. Once I'm 9 or more games out I'll still set the lineup, then sim the entire game. The exception is if I feel like my starting pitcher needs to come out I'll change pitchers myself and then I'll sim when my team is batting but play when pitching just to keep my eye on my pen guys. Once it gets to 9 games out, I just sim the whole game. If my team is in the playoff race all season, when I play teams that are 5+ games behind me in the standings I'll do the same thing as above.
Game by game keeps me interested in the stories of the season, lets me pay closer attention to my minor league system, and keeps me engaged strategically. Often times I'll switch teams if/when I get bored with my current sim. I'll look for the team with the best minor league system, or I'll pick the team that is in the worst financial shape with the worst system and try to fix that.
I also enjoy historical sims, which I typically do when actual baseball season is over. My favorite sims are taking over the Cubs in 1941 before WW2, just so some of the stars get their entire careers, or I'll take over an expansion team in their first season. I also like starting in 1977 because that was when I started collecting baseball cards or I'll start in 84, the Cubs first playoff season of my lifetime, or later in the 80's to get Maddux/Grace and Sandberg all on the same team.
Lots of ways to do it, that's what I enjoy the most. I'm also kind of a strategy/stats geek though.
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