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Pokemon has so many factors that go into making a personal experience that the idea of measurable difficulty is kinda silly. Obviously there are some objective things like one game giving important battles such as IVs and EVs while another game doesn't, but that doesn't really matter if the same player happens to use some of the best Pokemon in the former game and some of the worst Pokemon in the latter.
No two runs are the same unless it's a Sinnoh game lol so it all ends up fairly subjective.
