Risking a derail how is chocolatey nowadays? I really liked the idea but stopped using it because most of the packets were way behind the current versions.
Chocolatey is in the same space as the AUR (Arch User Repositories) in my opinion. It can be a hit or miss, but usually a hit. The support is fantastic when there's a bunch of users consuming the project as many users will contribute fixes to the package (e.g. packages for devs like node, cURL, git, etc). On the other hand, less popular packages will occasionally suffer from bitrot, though that all depends on the maintainer and whether or not the package has been configured to update automatically upon new releases.
Anything popular is up to date. But many windows programs have their own update methods anyway. So in some cases, you install the older version, but then update when asked.
