My own experiences aren't great with Windows, though they're smoother on OSX than Linux. The problem I have with Windows is that stuff does break, but it's inscrutable how and what to do about it, whereas at least on Linux there is usually some way to do something about it if you're tech-savvy. If anything gets borked in Windows, it's wipe-and-reinstall time; back when I used it full-time I probably did that once a year on average.
I find OSX to be poor for package management, though. I've gotten so tired of headaches with installing and managing updates of stuff, and badly interacting upgrades of the OS and separately installed packages and system versions of python/ruby/etc., that I do most of my dev work in Debian in VirtualBox now. In that aspect, it's Debian that's centrally managed with real release-engineering and integration tests, whereas OSX is an anarchic mess of 3rd-party software that nobody's responsible for integrating and testing.