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I think that your/you're and its/it's distinction causes no problem for sophisticated readers of English because the meaning is clear from context. Eventually there will be one spelling for both probably without the apostrophe. Usually, readers who learn this for the first time make a huge deal out of it.
It doesn't matter if it causes problems. That's not the point. The point is that if you're an entrepreneur and you make those mistakes, your customers may think that you're an amateur.
Or anyone else for that matter. If I notice a glaring error when using your/you're, my internal rating of quality of whatever it is I'm reading goes down a notch.

Is that fair? Maybe not. Could the rules be less arbitrary and confusing? Absolutely. However, when you type "your" instead of "you're", I have no idea whether you're doing it for that specific reason or if you're just somebody who didn't learn proper spelling in high school.

Another one I see all of the time is "there" being used for "their." Like fingernails on a blackboard (do those even exist anymore?) for me.