Same. I was a big Mac user through the 2000s, last one I bought was a laptop and 27" iMac in 2011. I wound up going back to Windows for multiple reasons, but of all things file management was as you say really irritating with OS X.
Then there's the value proposition which most speak of. A lot more for your money in the PC space, and if you want high quality build you can find that too - and typically still not hit Apple's price points. The big thing is the $900-$1300 price point IMO. There's nothing there from Apple but the MacBook Air. People can get a full on desktop replacement laptop with a good mobile GPU, useful for any task and far more storage in that price range with PCs.
I hate to say it b/c it gets over-used with the iPhone, but I really think most of the people with MacBooks are just showing off their hipsterism. If you want to show out in PC space, buy an Alienware - even those are a better value, and far more useable. I actually take a lot more note of someone with that alien logo on their laptop these days than someone with an dime-a-dozen Apple logo.