I have no quarrel with the notion that the rules of language should be reviewed, and completely agree that the purpose of punctuation should be clarity and disambiguation. To that end, I disagree that context should be relied upon to distinguish between singular and plural possessive.
I also feel that if something is confusing, education might be preferable to omission.
Where I have seen confusion with the apostrophe is not with respect to the possessive, but rather when the apostrophe is used for pluralization. "There are two ATM's at the bank". Although common, I don't think that apostrophe is proper. On the other hand, "There are four a's in the previously quoted sentence" is, I believe, a correct use of the apostrophe for pluralization.
Good Luck
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