Does くりかえし mean a single iteration or multiple ones?

Question

For example, in this sentence:

彼は、失敗をものともせず、 何度もくりかえし 挑戦し続けた。

くりかえし is modified by 何度も, implicitly stating that the action was repeated multiple times.

My question is that if the sentence was rearranged like so:

彼は、 何度も失敗 をものともせず、くりかえし挑戦し続けた。

does くりかえし then imply that the action was repeated only once (while the failures were multiple)?

Are there other ways to indicated the amount or frequency of repetitions (perhaps other than just with adjectives/adverbs)?

Bonus question: Does the first sentence indicate the "he" failed only once?

Answer 1

• The first sentence sounds fine, but the second sentence (more specifically the 何度も失敗をものともせず part) sounds awkward to me. I think I'd rather say:

  "[度重]{たびかさ}なる失敗をものともせず・・・".

  Maybe it's because 度重なる is a 連体形 verb and modifies 失敗, while 何度も is an adverb and "何度も...ものともせず" sounds awkward... Maybe when 何度も modifies a negative verb, it's interpreted as a partial negation. Like, 何度も[諦]{あきら}めなかった sounds awkward to me, at least it sounds ambiguous between "諦めない happened many times (=negation of 諦める)" and "didn't give up so many times but did give up maybe once or twice (=negation of 何度も諦める)".

• if the sentence was rearranged like so:

  彼は、何度も失敗をものともせず、くりかえし挑戦し続けた。

  does くりかえし then imply that the action was repeated only once?

  No, くりかえし~~し続けた implies that the action was repeated many times.

• Does the first sentence indicate the "he" failed only once?

  No, the 何度もくりかえし挑戦し続けた implies that he failed many times.

• 彼は、失敗をものともせず、何度もくりかえし挑戦し続けた
  彼は、失敗をものともせず、くりかえし挑戦し続けた
  彼は、失敗をものともせず、何度も挑戦し続けた

  all sound fine to me. 何度もくりかえし sounds to me as an emphasis on 何度も or くりかえし, "many many times, again and again". I think the 続けた already implies that he failed and tried many times, so even 彼は失敗をものともせず挑戦し続けた sounds alright to me.

• くりかえし is modified by 何度も

  Hmm I'm not sure... I'd rather think that both くりかえし and 何度も modifiy 挑戦し続けた. (Because 何度もくりかえし挑戦し続けた and くりかえし何度も挑戦し続けた both sound alright to me.)

Answer 2

I don't think you understand the sentences correctly. The two of them are quite different.

First, notice that くりかえし is a verb in 連用形 (the verb くりかえす "to repeat"), not a noun.

Your first sentence (awkwardly) reads ignoring failure, he kept retrying to take the challenge several times.

Your second sentence reads ignoring several times failure, he kept retrying to take the challenge. It seems that at some point, he did not ignore failure, but still kept retrying…

何度も modifies the verbs くりかえす (as くりかえし) or する (as せず), not a noun, as your usage of bold and your question seem to show you thought.

Also, because of 続ける, we know that retrial did not happen only once. Would you say "Ignoring failure several time, he kept retrying only once"?

To sum things up, I think that the question is meaningless, and I hope that my answer helped you understand why.