In terms of tone, I reckon it only matters to a point. Playing with a dude who is using a cheap Ibanez shred guitar into a solid state amp with a ratty distortion the whole time... that's when I notice and think, "You could really have better tone." But most of the time, if the people I'm playing with are competent and their gear isn't Samick/Ashton level, I don't notice or care. And when I've asked people about MY tone I've realised that they don't really care either.
That being said, I still enjoy the tone quest.
For myself, I got to a level of playing where I'm competent at playing in the environments I play in: church, and covers bands. And then I realised, I don't actually really WANT to be Guthrie Govan. I'm just a lazy guitarist, I guess! But I treat playing guitar like a hobby, alongside the other things I like to do... reading, listening to music, playing a few games. Every now and then I have a fit of practice, where I'll try to improve a particular technique, but even then it's mostly just fun. I have no pretensions to make it with a band (I enjoy my day job). I just want to play competently with friends here and there, and jam along to music in my study at home.
So for me guitar is a fun hobby and gear and GAS is a part of that fun. I like trying new stuff, I like chasing that perfect sound that only I will notice.
So for me the TL;DR version would be: I am well aware it's not the gear that's to blame when I don't sound good, but the gear quest adds to my enjoyment of guitar as a hobby.
And I don't think "I don't care" so much as I think that everyone's just got different goals and aims with guitar, and different things they enjoy, and that's all good.