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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 ...


Among these scenarios, 5匹目が好きです makes sense only in Scenario 3. 5匹目が好きです never means "the fifth smallest cat" in any of these situations. "The fifth smallest cat" is translated as 5番目に小さな猫 in Japanese (general rule is found here). If you say 5番目に小さな猫が好きです, it's at least a valid and understandable Japanese sentence. Of course, a normal person will never say ...


彼は新しい車をほしがっている can mean He wants a new car (= …車が欲しいと思っている) He is showing his desire for a new car 彼は新しい車がほしそうだ means "He looks desirous of a new car". 彼は新しい車をほしがっていそうだ is usually taken as something like "I assume he is now begging a new car".

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