Actually, explaining how to get Python working on Windows is far, far easier than on either linux (modulo various distros) or the Mac. That's because there is one obvious distribution of Python to use, the official one, and new versions of it are always consistent and play well together.
Yes you can use Anaconda if you want, and people who do that are probably data scientists or something and know what they want to do and why. It's well documented and has it's own robust ecosystem.
I say this as someone who's been on Macs at home since 2007 and works professionally on Linux, but I started with Python on Windows back in 2002.
Unfortunatly windows has plenty of problems too. First, the system PATH will kick you if of you have more than one python installed, so the official installer does not add to it by default, hence the python command doesn't work after an install. Instead, you get the py launcher, but it's not provided if you installed python from the app store or with anaconda.
". . . and then he installed cygwin, and decided to manage and run python through the bash environment. . . " (fun fact: the git client's bash shell is actually cygwin. Also; MobaXTerm has cygwin bundled-in as well).
