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As I was thinking some mock conversations I tought the next phrase:

この漫画は友達が日本に行って買って来てくれた

Does it get confusing, weird or unnatural linking four verbs like that? (I can't remember hearing/reading something like that).

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Grammatically, your sentence is already perfectly correct. The verb part consists of two actions (行った and 買ってきてくれた), and there's nothing wrong or unnatural about using two or more subsidiary verbs. However, this sentence may carry an unnecessary implication that your friend went to Japan specifically for buying this manga. If your friend visited Japan for another purpose (e.g., sightseeing) and bought the manga as a souvenir for you, it would be safer to say either of the following to avoid potential misunderstanding:

  • この漫画は友達が日本で買ってきてくれた。
  • この漫画は友達が日本に行ったときに買ってきてくれた。

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