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IMO managers and GMs should be a lot more variable than they are now, or at least have the option to make them a lot more variable. This would create the kind of universe the OP is talking about. Right now even GM's who are very opposed to each other, on Rebuilding vs Win now teams, still largely value the same thing and play the same way.
I've got another reason for liking this, too. What would happen over time is that strategies which don't work will fade away as unsuccessful managers/GMs are let go and winners get to stay around. Strategies would come full circle as new GM's and managers take advantage of players who are undervalued in whatever the current universe style of play is.
How would such a league evolve? Maybe we'd see that the optimal play style isn't quite what we thought, and the AI would become more and more challenging. In an indirect way it will let the AI learn.
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