I don't think the goal is to sim any games, but being able to set and size/length because simming is an option, is a positive for whatever we decide to do.
As long as those with commish power (please dear god allow more than ONE!) then simming could ultimately NEVER happen.
Someone can't be available? Ok, boot, opponent plays CPU, and the league doesn't flinch.
Because of these factors, I'm more partial to the longer season because I prefer having mini-series vs your opponents, multiple ones, I'm not in a rush to finish it.
It really doesn't matter if half the guys who start this league flake, if this league comes down to the 6 or so guys who we know won't quit, because you can always progress and play your games now that CPU is enabled. I personally have no problem with that.
So having said that, length is ultimately up to us, but shouldn't be viewed as a "concern" that may destroy the league because it no longer can from the sounds of it.
Personally, my ideal VSN baseball season would look like this.
March - 4 Week long Release Day roster tournament.
April, May, June - 30 Team, 10 Week long reg season (3-4 games a week), with 2 week long playoffs (using opening day or whatever rosters we like)
July, August, September - Same as above.
Again, just my preference. I wouldn't care if it was just 6-10 humans and the rest CPU, lot easier when you don't have to match up with a human every time for scheduling.