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I picked up the following phrase to say "I hope you are well":

うまくいきますように!

Looking this up in a dictionary, it seems it could become:

上手く行きますように!

Is this correct, or is it better to leave out the Kanji-fication?

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    Problem is 「うまくいきますように!」 does not mean "I hope you are well." in the first place. It is not a matter of kanji vs. kana. – l'électeur Sep 10 '17 at 12:00
  • Ah...excellent... That would explain a lot, and it highlights the pitfalls of using phrases online! What does it mean...? Hopefully nothing too offensive... – user3379824 Sep 10 '17 at 12:07
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    @user3379824 It means, roughly, 'I hope it goes well', or 'I pray it goes well', not 'I hope you are well'. – Aeon Akechi Sep 10 '17 at 14:58
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A rough¹ count of the results in the Balanced Corpus of Contemporary Written Japanese (少納言) gives the following numbers

上手くいく   274     8.2%  
上手く行く    93     2.8%  
うまくいく  2742    82.4%  
うまく行く   220     6.6%

leaving out rare (<1%) kanjifications such as 旨く行く.

¹ I checked い・く and 行・く for the following conjugations: ~く、~か、~っ、~き, but didn't check the individual results for false positives.

These numbers clearly suggest Not To Kanji for うまくいく (as a general rule — writing by numbers is just like painting by numbers, i.e. not the height of the art).

うまい itself has slightly different numbers, but still suggesting Not To Kanji:

うまい    11153    79%
上手い     1837    13%
旨い        665     5%
巧い        238     2%
美い        167     1%
ウマい       58     0%
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Personally I don't think it makes a huge difference to use kanji or not for short phrases like that, but its good to use kanji if you have a massive wall of text because it can make it easier to digest and you can get the meaning quicker than by parsing every hiragana character one by one into words

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It depends on your audience.

For anything longer than a simple phrase, the only place you'll see all hiragana is in children's books. But newspapers use more kanji than most people sending IMs to each other. Even then it can depend on the person. And not just education level, but individual idiosyncrasies.

Really, it comes down to experience. You send and receive enough messages until you get a sense for what words are not written in kanji even though they exist, what words are almost always written in kanji, and what is considered a good balance between kanji and hiragana when a lot of the words could go either way (think daily conversation level).

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