My first Mac was a 17" Powerbook G4 1Ghz, sometime in 2001. While I absolutely loved the hardware, I remember initially HATING the OS because I couldn't find anything (as I was used to the Windows ME nightmare).
Once I learned the OS I figured that it was way more intuitive, and I've been using Macs exclusively in my personal life ever since. It led to annual 17" PB/MBP upgrades, a G4 Cube, a PowerMac G5, every "iPod iMac" until 2011, white iBook, white Macbook, and several 13" and 15" MBPs.
Pure computing bliss, from the OS to upgrades and maintenance.
My current Mac setup is a 2011 Maxed-Out 27" iMac, a 2011 17" MBP, and a 2012 15" MBP with the Anti-glare hi-res screen.
Sadly, unless the mythical modular Mac Pro blows me away, it looks like they'll be my last Macs, due to the advent of the current Seal, Solder, & Dongle Age.
I'm already working on a PC buildout project that will be hackintosh-compatible, but I'm more than pleased enough with the Win10 and Android/Google Services combination (via work-provided devices) to give up on Apple entirely.