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1) IIRC, the scheduled number of games will change, not the monthly length. It's somewhat random in terms of when it changes and how often. Or if it ever does. Personally, I leave automatic evolution off as I find it's just not realistic enough.
2) I will usually sim a fictional league for a decade or so before jumping in. That gives ample "burn-in" time and also gives the league finances a few years to stabilize. I like to have a little history, and it gives me a better base for evaluating the players. I've never "wiped" a league after doing that, though.
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