Im not sure lots of people know this about DQ....but here are a couple tips if you are struggling.
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You don't have to play the first stadium as soon as you are on it. If you hit the back button it will take you to the board and you can continue past it. This allows you to play all the showdown moments and increase your chance on lower difficulty levels when you come back to it.
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If you already have Kenley and just need Santana, you can use step 1 and jump over the first two stadiums and only play the 3rd and quit after you win and receive Santana.
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Losing to the zone sweeper doesn't end your quest, you'll just lose 50% of your DQ currency and receive a penalty card. On the next showdown you play, that red card will be gone.
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Be sure to use guys with high vision. This helps with your swing timing on higher difficulties.
Sorry if everyone knew all these tips, just trying to help those struggling