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Yes, the playoff format will naturally evolve with your league in real time. Only caveat here is I have "Automatically expand league" and "Automatically adjust league strategy when advancing to next season" checked in settings, under league settings and historical.
You obviously have to check the first box to get expansion. I don't know if the second is required for playoffs to change as I've never tested, but it might be the case.
One thing to know on this as I think you said you're relatively new - a GREAT suggestions the real vets on here make all the time is create the game you want, save a copy of it (either backup through OOTP or just copy/paste in windows explorer) and then run your sim for 5-20 years, depending on what questions you have. I personally stay away from looking at results like who won championships or my org's records as I don't want to know the future in OOTP - up to you - but you can go in and check historical accuracy, see what the playoff format is set up as now, etc. It's a great way to make sure you don't go a long way down a path in a game you care a lot about, then find out there's a hole you had no way to solve and you have to start over.
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