Since Apple has given up on keeping what really matters for a Unix, its tools, up to date the amount of time you have to spend installing the latest version of things like Bash is actually higher for OSX than Windows these days.

I am aware that at least one of the reasons for Apple to ship stone-age versions of everything from Emacs to GCC is that they hate GPL3. But the reasons don't matter when the latest version of their operating system is unable to run modern software without installing a set of packages that more or less replaces all of the Unix tools. When you have to do that, it doesn't really matter if you install those tools on top of Windows or OSX.

As for myself I find Windows to be absolutely unusable and I was using Linux up until around 2002 when I switched h to the Mac. Lately however, Apple's utter disregard for technical users that prefer the Unix experience has made me switch back to Linux, and while Linux has issues of its own, at least everything works out of the box without having to deal with an entire separate ecosystem of packages on top of what is provided by the operating system itself.