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。
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?