Really enjoyed the episode.  I've known about Chocolatey for some years now and it's been a godsend for me when I have to use Windows at work (I primarily use Linux and OpenBSD).  I actually have a scheduled task that runs the "cup all -y" command daily (this command sequence upgrades all packages installed via Chocolatey and accepts all prompts).  I also use MSYS2 for a proper Unix-like shell with pacman for running updates so that I can use all the CLI apps I use on Linux/OpenBSD.  PSTools is another suite of tools that I can't live without.

Ultimately, one needs to use the tools that work for them, whatever that is.  If it's Windows or macOS, great.  If it's Linux or a BSD or something completely different, great.  If it's TempleOS, I'll have to raise an eyebrow, but still, great. :-)