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I'm actually going to suggest against starting with a modern MLB team. In that case all the 'bells and whistles' are on - waivers, DFAs, minors and so forth, and it's very easy to get lost.
For starting out, I recommend historical play: Less rules, less players. As you grow more comfortable you can start adding in rules during each postseason.
As an alternative, there is a fictional quickstart included with the game about mid-range in difficulty.
1. David answered your question admirably. Given your APBA background, if you're really interested in season simulations, I'd turn on historical transactions, and recalc on a 1 or 3 year basis. Anything else is fantasy or 'what if' (which is the mode I prefer.)
2. Again, David answered your question well.
3. Your fantasy scenario (Cobb, Speaker, Jackson) is entirely possible. The big catch is 'making the trade they were offered in 1908.' The AI may not want to. Of course, you could go into commissioner mode and force the issue.
Jackson will not automatically be banned/'retire' unless you have the 'retire according to history' box checked. Nor will any of the other Black Sox.
4. le receveur answered this. As he said, this avoids preconceptions about characters. For example, I might be disappointed if I started your fantasy scenario and Jackson just didn't pan out (injuries, bad die rolls, what have you.) I wouldn't mind as much with a fictional. Further, it lets you play with dream scenarios: Want to start a league in Canada? Or the Moon? Then fictional's for you.
5. I'm guessing here you mean multiplayer leagues. My advice would be to find one that's stable and has been around awhile, and one that is new player friendly. Sometimes these leagues will offer you a mentor - another GM to make sure you understand what's going on and don't make too many mistakes.
Lastly, by all means experiment. It took me a few VERSIONS to become fully comfortable with the game, and even now I still have my moments. There is A LOT going on.
It may help to remember that there's a solid core to the game (the baseball simulation), and everything else is just attached. A lot can be turned on or off depending on your league's needs and your confidence with the game.
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