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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 ...

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