I've recently seen several articles containing the phrase 記｛き｝者｛しゃ｝泣｛な｝かせ. All the articles have been about unfortunate events, and 泣かせ clearly means something is making somebody cry. My question is how do you use it.
One article says 取材を受けた時に、声もごく小さく、記者泣かせだった。
Does that refer to the entire event as a 記者泣かせ？ Or referring to the person with a small voice as a 記者泣かせ？
On a different website it says あなたは正しく書ける？ 「キヤノン」や「ビックカメラ」が新人記者泣かせな理由.
Again - who/what is the 記者泣かせ describing？