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I'll take a small stab at this, but your best bet is to just play some to familiarize yourself. The game will prompt you for the big, in-season events such as the draft or the international signing period.
I personally don't use the waiver wire too much in single player, but it's worth checking every time your sim gets stopped (for injury, personal message, etc.).
A 25-man roster is in no way intended to get you through the season. You essentially have 15 reserves (40-man roster) that can serve as fill-ins in case of injury. Once on your 40 man roster players can transition between major league team and minor league team freely four times. Once a player has exceeded the number of "options" he must clear waivers to be demoted a fifth time.should you want to clear a guy from your 40-man roster, you would also have to clear him through waivers. This is how the Waiver Wire is populated.
The most traditional times to make a trade are 1) during offseason, 2) very beginning of season or 3) close to trade deadline (end of July).
Hope that helps a touch
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