IronWolf
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Interesting question. My guess is that experience will generally help, but I'm not sure that having an "old school style" is a strict positive or negative. It's probably a positive for some groups and a negative for others.
I think this is likely the most accurate. Experience playing RPGs helps. I suspect more than the "old school style" helps. It just happens to be that a lot of people with a lot of experience can say they played the "old school" games because their experience goes back that far.