口語は必ずしも正しい文法ではないから上手く翻訳されないことが多いですよね。I can’t quite translate it. Can you help me? What does しも mean?
This is basically what I understood: “Since, the spoken language is not necessarily grammatically correct, there are many things that can’t be translated well.”
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必ずしも means “not always” when paired with a negative (ではない in this case.)
So yeah your translation is correct more or less. Since, the spoken language is not always grammatically correct, there are many things that can’t be translated well.”
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Thanks for the quick response.
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Its what I do, I’m not a slacker like that Leebo guy!
Here is a site with more examples on how to use it if you want to give it a look to maybe help you remember, but it seems like you got the other use down pat for the most part.
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Wondering about the く where I would have expected に. Any thoughts?
Converting a na adjective into an adverb does indeed require you to tack on a に. 上手い, however, is an い-adjective.
The rules for converting an い adjective into an adverb is simply swapping the い out for a く. Does that clear it up or are you not clear on how I know its an adverb to start with?
EDIT: Ah I see your confusion maybe. You may have been thinking of じょうず which is 上手 and indeed is a na adjective. Pretty confusing. 上手に(じょうずに) is a more polite way to say the same thing more or less, but as you can tell by the conjugations in the sentence, this isn’t spoken in the most polite of ways. 上手い is also read as うまい rather than じょうずい or anything like that.
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I am clear about the rules for adverbs, but I didn’t know 上手 could be an い-adjective, too. But looking it up on jisho I see that it could be read as うまい、which I have heard (and read). Is it a weird choice to write it in kanji?
Edit to say I read your edit! 
Hmm, not really, and it appears 9 times in the first volume of this light novel I checked so its definitely good to remember it can be written that way.
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It is good to remember, but if you encounter it 9 times in one novel, that is still only one sample (same author, deliberate style choice).
Anyway, I am sure I will remember the next tkme I come across it. Thanks!
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I checked a visual novel and found it 159 times!
上手 came up 64!
I have too much free time!
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I’ll just add that I also see 上手い pop up quite often as well.
I know this because I always read it and go “じょうず…い…? no, that’s not right” 
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I just remembered… one of those places was actually in a chat message I recently received, which seems to indicate that it’s pretty common in everyday writing as well, not just in books.
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