Parallels’ way of handling USB is just perfect. I was trying to install RockBox firmware to my iPod Classic and the easiest solution was to use Windows XP in parallels. That’s when I realised how well it’s implemented! It first asked me if I wanted to attach usb with Windows VM or MacOS, and later I could even make it default. Very good UX.

Edit: Windows XP, because I still remember its Product Key. Ha. I probably reinstalled XP in my PC as a kid about a hundred times.