My inner type snob got a bit hung up here, truth be told.
Prime and double-prime — don’t use apostrophes to denote distance (I’ve never looked at bridge clearance signs the same way). Sometimes straight-quotes are used to differentiate between prime (not part of the standard keyboard, technically, as primes are slanted) and curly-quotes and apostrophes.
Also, apostrophes, technically, are used to denote omission of one or more characters and possessive — hence y’all’s is typographically correct (possessive, omits the “ou” from “you”).
It’s also why ’90s is correct while having the open-single-quote instead is incorrect (we are omitting the “19”). Note: Medium’s text editor is the first rich text editor I’ve seen that does this correctly (last time I used MS Word, it did not do this correctly, and neither does Apple’s Pages.app).
Good read all around though. I definitely concur.