Just a few suggestions regarding scaling.
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Have scaling only apply after a user’s first time through. (ie, on subsequent plays) - This allows a broad range of players to get through the content, but keeps the battle for top prizes competitive.
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I like the hard and easier modes. If you restrict entrants based on level (ie, only characters level 85 or lower allowed in easy mode, characters say 60+ playable on hard mode) you could then tone down the scaling in easy mode to make that more competitive.