In 2008 when I did rails I was always annoyed that the dev tools heavily favored mac but you deployed to linux. No end of issues with native gems and deploys. I don't think I was using windows back then.
I hate this. Some tools work best on Linux (i.e. LAMP/LEMP, composer, etc. - performance is noticeably better than Mac). I don't even mention Windows here because it's probably worse. I'd love to have one ultimate OS to do web development, but find myself hopping to Linux and back to Mac... and occasionally to Windows (games :D).
Mac/Windows with Linux VM solves this issue, but it's a hassle. Windows Subsystem for Linux is again very slow (try composer) because of slow I/O -- so that great attempt from Microsoft doesn't work for all.