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？
記者泣かせ literally means "thing that makes writers cry". 泣かせ is a masu-stem of 泣かせる ("to make someone cry") and it works as a noun. ～泣かせ is an idiomatic expression that means "source of headache for ～", "bane of ～".
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？
It's unspecified. I think this can be interpreted both as "It was a 記者泣かせ event" or "He/She was a 記者泣かせ person". It doesn't have to be distinguished strictly, either.
「キヤノン」や「ビックカメラ」が新人記者泣かせな理由
In this case, these company names themselves are the source of headache for novice journalists. Simply, these words are very commonly misspelled (×キャノン, ×ビッグカメラ).
