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Does there need to be some mistake in order to use the ~なおす suffix:

宿題をやりなおしなさい。// ok (but there needs to be at least one mistake)
料理を作りなおした。 // ok (but there needs to be some fault)

Regardless of whether there is a mistake, you just cannot say:

宿題をやりかえしなさい。// never ok
料理を作りかえした。 // never ok

Could I say something like:

(1) 昨日、好きな曲を何度も聞きかえしていた。 // Last night, I listened to a song that I like many times in a row.
(2) 昨日、好きな曲を聞きかえしおわれなかった。 // Last night, I couldn't stop listening to a song that I like.

I really do hope #2 is correct and natural. It sounds good to me, but stringing 3 verbs together just seems too extreme. It can't be correct?

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    Lacking enough conviction to put my gut feeling to an answer, ~かえす is more about repetition and ~なおす is more about redoing; an encore vs a do-over? :D – Brandon May 4 '16 at 20:10
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As Brandon says the suffix, なおす means “to redo” as its Kanji writing “直す” means “to redress, correct” and かえす means “to repeat” as its Kanji writing “返す” means “to return.”

Your example (1) 好きな曲を何度も聞きかえしていた is alright. It says you were listening to your favorite song repeatedly.

But (2) 好きな曲を聞きかえしおわれなかった sounds odd and strange to me. Though I don’t know what you’d like to say, from your English translation, perhaps you’re going to say either “好きな曲を繰り返し、(楽しくて)聴くのを止められなかった” or “好きな曲を何度も聞き返そうとしたが(時間がなくて)できなかった,” or simply “好きな曲を何度も繰り返して聴いた.”

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