Will we ever do away with apostrophes in its, youre, lets, wont, cant, etc.?

Answer 1

Interesting question. While some words like "can't" could exist fine without the apostrophe, other examples you give such as "let's" seem to need them. Without the apostrophe, "let's" becomes a different word, as in "I hope she lets him down gently." "We're" is another example of a strictly necessary apostrophe since "were" is a totally different word.

Essentially, I think the more possibility of word-confusion without the apostrophe, the less likely it is to be dropped. "Won't" is a long way from "will not," but there is the word "wont" as in, "As I am wont to do." That said, in context these probably wouldn't be confused too much.

Probably the more you think about them, they all might be confused for another word. Languages change pretty fast, but it's hard to say how this will occur in the internet age. Correct language is more accessible than ever, but informal typing has also grown dramatically. It will probably depend more and more on who you ask and the writing conventions of different areas of society.