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I was reviewing some N1 Grammar when I noticed that both of these seem to translate to "when it comes to", "as for" Is there any difference between the two in terms of nuances? I'd really appreciate it if you can cite sources.

https://japanesetest4you.com/flashcard/learn-jlpt-n1-grammar-%E3%81%A8%E3%81%8D%E3%81%9F%E3%82%89-tokitara/

https://japanesetest4you.com/flashcard/learn-jlpt-n1-grammar-%E3%81%AB%E3%81%84%E3%81%9F%E3%81%A3%E3%81%A6%E3%81%AF-ni-itatte-wa/

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Xに至っては has the nuance of "moreover", "on top of that", "what's worse/more", etc. It means X is even more extraordinary than what was already mentioned. The examples in the linked page lack the context, but 美智子に至ってはうきうきしているようだった makes little sense without a proper previous context, like:

その悲しいニュースを聞いても、太郎は特に悲しんでいないようだった。美智子に至ってはうきうきしているようだった。

Xに至っては also means "now that we have reached X", "(we're already) at this point", etc. 「ここに至っては、もう祈ることしかできない。」

Xときたら is just a colloquial topic marker, and the predicate is usually something bad. It's typically used to speak ill of something/someone, as shown in the examples in the link.

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  • Thanks @naruto! Does it mean that に至っては has a similar meaning to おまけに?
    – rebuuilt
    Apr 16 '20 at 2:44
  • @rebuuilt おまけに is different because it implies the modified sentence is less important (おまけ basically means "bonus/extra").
    – naruto
    Apr 16 '20 at 2:47
  • That's interesting. Japanese can be really complicated at times. I asked this question because I saw somewhere that おまけに can translate to "to make matters worse" japanesetest4you.com/flashcard/…
    – rebuuilt
    Apr 16 '20 at 2:50
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    @rebuilt Okay, "less important" was an overstatement; おまけに can be used to add something equally bad, too. But Xに至っては only means X is even extreme. For example 「値段も高いし、おまけに味も悪いが、サービスに至っては最悪中の最悪だ。」「彼は勉強もできるが、スポーツに至っては県代表クラスだ。」
    – naruto
    Apr 16 '20 at 3:02

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