dtgreene: Actually, as far as I can tell:
* A possessive *noun* needs an apostrophe: "John's", "Mary's", "the table's legs" (note that "legs". when the plural of "leg" has no apostrophe, but the possessive "leg's" does need one)
* A possessive *pronoun* does not have an apostrophe: "his", "her", "its", "my", "your", "their". Notice that these forms tend to be less regular; many don't even end with an "s".
* It just so happens that "its" has a homophone "it's", which is a contraction that is equivalent to "it is". Similarly, "their" has homophones "there" (a term used for a location) and "they're" (contraction for "they are"). If you notice, many of the common English mistakes involve using the wrong homophone in writing; in spoken language, this mistake doesn't exist.
* Some dialects of English have nonstandard contractions like "I's" (I is) and "ain't" (am not); these contractions are not homophones of standard English words, and therefore tend not to be used accidentally by people not using those dialects.
Yes, the confusion is complicated because, in English, an apostrophe indicates both a plural (noun) and also the omission of letters, as in the word
fo'c's'le (
videlicit, the pseudo eye-dialect phonemic transliteration of the crew's living quarters below decks in the bow — known as the
forecastle, but pronounced as per the apostrophes). In this instance, the apostrophe/s indicate a contraction in an aid to pronunciation.
Yet another (completely contrary) use of the apostrophe is to indicate the plural for of a borrowed word. This is probably the genesis of the dreaded greengrocers' apostrophe, as they were merely introducing a foreign word to their customers, hence
banana's means "several of a tropical fruit new to Elizabethan England (and Modern English)", which were never seen before Cavendish imported them.
As has been noted, these grammatical peculiarities are not a problem in spoken idiom; literacy had penetrated less than 2% of the populace until modern times.
A lot of modern vernacular writers use nouns adjectivally. (This is especially prominent in the USA:
California raisins, instead of Californian, for example.) Is suspect this is yet another idiomatic adaption, either by the monoglottal Anglophones (as a mistake) or the polyglottal migrants, to lessen confusion (between noun and adjective forms of a word). (If I had to bet, I'd wager the monoglots are at fault, since their language skills are significantly impaired.)
English really needs some consolidation (and ingenuity) in its use of punctuation. Unfortunately, literacy, punctuation, and spelling all fossilized with the appearance of Modern English. However, that doesn't mean new idioms cannot develop; the subtle difference between
imply and
infer was only militated in the 1970s (so, for example, Jane Austen is blind to it). (And, on point, the use of an apostrophe to indicate a decade, as in
1970's, has dropped out of fashion in the meantime, too.)
Also, to answer the OP: it depends.
If the mistake is buried in a log where it's not easily visible, then, No. (It will bug me, but as long as I can distract myself playing, then I can ignore it.) Far more catastrophic, for example, is the missed apostrophe in the VERY FIRST LINE of the beginning of
Dex. I have lost several microns of tooth enamel from my molars because of it. :)