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From my dictionary, masu-stem+あぐねる seems to imply that you get tired of doing an action because you have met a setback that prevents the result you hoped for from occurring despite various efforts.

In addition, it seems to imply this is based on an accumulation of a realization that things are not going well and that you are in a dither. From this, it says it is not used with instantaneous actions or things that happen once, and they use this example:

❌ゴールキーパーがシュートを取りあぐねる

Question 1: how long and how subjective can this span of "things not going well" be?

How long does someone need to fail with coming up with a plan generally before they can say that they 考えあぐねる?
How long do you need to waver over what to eat for lunch before you can say you 決めあぐねる?

Question 2: is the part about things not working out in spite of efforts always present?

My impression is that with coming up with a plan efforts would be included, but probably not so much when deciding what to eat for lunch. In the latter case is it a kind of hyperbole?

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You seem to have already consulted a dictionary, so let me just answer your specific questions.

Question 1: how long and how subjective can this span of "things not going well" be?

It's very subjective. It can be several seconds (such as in "3人のディフェンダーに阻まれ、攻めあぐねてバックパスを出した") or many years (such as in "遠い国にいる思い人を待ちあぐねている").

In the case of 考えあぐねる or 決めあぐねる, you typically need to think for at least a few minutes before saying this, but it can be much longer or much shorter depending on how important the problem is and how urgently you have to make a decision. The time I would imagine when hearing 決めあぐねています obviously depends on whether the speaker is deciding on a lunch menu or a marriage partner.

Question 2: is the part about things not working out in spite of efforts always present?

There's usually a nuance like "running out of other options" or "not knowing what else to do", but this does not mean you have to make proactive or visible efforts. In the case of 待ちあぐねる, all you do is worry and wait.

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