My sense is that if you asked 10 people here randomly, usually about 8 of them (at least) would say to sim ahead 20 or more seasons to establish a history for your league (and, I suppose, to make sure your settings are yielding the results you are looking for and something isn't fatally flawed.)
But I would be one of the 2 who wouldn't say that. Actually, I'd say do what feels right to you. But I started my OOPT fictional universe from the beginning because I like to be in on the ground floor and I'm a bit of a completist. So if I'm going to engage in a league, if I'm going to take control of a team, I want to be there for all of it.
And that's worked out fine for me so far.
Still, good reasons to do it either way.
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