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Hot take: the apostrophe serves no useful purpose, and we just shouldnt bother with it at all. Or, we 'should alway's include it before every 's (or ju'st make 's be how we write the letter 'sometime's, like with ſ)
(inspired by https://twitter.com/FakeUnicode/status/1201478752024137729?s=19 )
Gonna just make it part of my personal writing style that I dont use apostrophes. I dont think most people would even notice. If the New Yorker can insist on the umlaut thing, I can insist on not using apostrophes. Or the word "whom".