Earlier quoted context omitted.
You lost me at "it's". Perhaps standard grammar is not, as you argue, the best measure of semantic correctness. Then please, let us violate standard grammar wherever it improves accuracy. Writing something different from what you mean because the two sound alike does not qualify. I'm fond of Bertrand Russell myself. Does your argument stand on its own?
If we were to replaced both "it's" and "its" with just "its", absolutely no expressiveness in the language would be lost. This is shown by the fact that in spoken English, there is no audible distinction between these words. You can tell which word is being used 100% of the time that they are used in a sentence by the context alone. No sane person ever argues that we should introduce an audible distinction between "i…
Perhaps a new standard of spelling could be created and, as you suggest, "it's" and "its" could be replaced by "its." But that's not what you're doing when you write "it's" instead of "its;" instead, you are writing a word that is different from the one you mean.
"Its" has a meaning now, today, that whoever parses you language will use. Perhaps you will convince everyone to overload that meaning with a new one, but in the meantime write what you mean.