I must say it matters to me.
I usually notice whenever I read a misused apostrophe. Of course in most communication it doesn't actually matter, but I still notice.
However, should it be in a formal letter, a CV, an application or any other written communication of import then I think it comments on the effort put in to that communication by the author.
It certainly feeds into my opinion of the document and therefore the author. Along the lines of "if you don't care enough to put the effort into writing it, why should I care enough to put the effort into reading it?".
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The Apostrophe Society has Left the Build.. new
The Apostrophe Society has Left the Buil.. new