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The first season will start on opening day but after that it will go through offseason, preseason, spring training, etc.
Personally I tend to play in GM mode most of the time - some people like to get into the details of running each game but the game supports any kind of playstyle you want. You may want to let the manager run things for a while and jump in and handle a few games here and there till you get a feel for it.
You can start in the minors and move up, however I have found it frustrating as you can't really control when you get moved up (tends to be after you do well for a few seasons) and I end up wanting to manage in the big leagues sooner - but it is an option. You can of course have as long a career as you want in the majors.
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