As a constant analyzer, I thought on it and tried to break things down into reasons that made the most logical sense to me (also, trying to find out if I was actually a grammar Nazi) - someone bothered by and must correct grammar faux pas wherever they might be. I realised that most things don't actually bother me as much as the interchangeable usage of "your/you're".
So here's what I learned: "You're" is referring to something that you are. Like, "You're beautiful". "You're amazing". Or even, "You're a grammar Nazi". Whereas, "your" refers to things you have. Like your shoes. Your heart. Your desire to understand the difference between words that sound similar.
Why does this difference matter to me? Because on a fundamental level, I think it is important to know the difference between something you ARE and something you HAVE. To me, that is a HUGE difference - especially on my own personal journey and discover of who I am.
I guess it could be argued that to have beauty and to be beautiful are basically the same thing and perhaps I am grasping at subtleties but for me, when you HAVE something means it can be lost or taken away but when you ARE something, it is with you always.
When someone texts me, "your awesome", I will still always think to myself, "my awesome what?" but will resist correcting as best I can and just take the compliment because I'm sure you didn't just forget to finish the sentence and that you actually meant to tell me that I AM awesome not that I HAVE awesome... which is nice to be told so let's not get so technical - I appreciate you xo. Also, to have awesome works too so maybe not the best example - moving on.
And for those who might be using "your" as a shortened version of "you're" - "ur" is the shortest way I can think of that still makes the distinction - just throwing that out there.
Another good reason I can think of about the importance of knowing the difference is for basic sentence structuring.
"You're the most amazing person I know. Your compassion, and humour blows me away every time we interact. You`re kind and loving when you offer your welcomed words of wisdom. I can see why you`re loved by many. I love you. I miss you. Bring your sweet buns over for a visit soon."
Important grammar distinctions at a glance:
to/too - "to" = destination, "too" = also or as well
we're/were - "we're" = we are, "were" = past imply
their/there - "their" = talking bout people, "there" = a location
where/wear - "where" = location wonder, "wear" = on someone
Quick conclusion:
The English language is confusing.
*I am by no means a professional in any field of literacy nor claim to be an expert. I simply am displaying my own particularities towards distinction and accuracy of a few words because I'm weird like that.