Chocolatey is a mixed bag. Since it is basically just wrapper scripts around upstream installers, it very much depends on what the upstream installer does. To me, it acts less like a package manager (apt) and more like a rudimentary installer runner.
This causes all kinds of annoying usability issues. Chocolatey doesn't know if you uninstall via Add/Remove programs, or update via standalone or self-update mechanism, and will just show incorrect install and/or version info, and fail to upgrade properly. A lot of packages don't even install the version that Chocolatey says, but instead just install the latest at time of install.
Scoop is way different, and has none of these problems. Funny enough, they describe it as "not a package manager" but it feels way closer to apt to me. Everything is essentially a portable version of the app, and it puts them in ~/scoop/apps/[name]/[version], creates a junction (symlink) to ~/scoop/apps/[name]/current, and adds executable "shims" to ~/scoop/shims (which is in the user's path). There's no Windows "uninstall" entry, no versions to be desync'd, and no hidden garbage that can sneak in.
I gave up on chocolatey (though some software from google relies on it to build). Have been using WinGet for a while, but feels bit underwhelming, and at work already several folks have recommended scoop - I guess it's the time!
