Yeah, it got a lot better in the past few years. It was disaster 5+ years ago, as NO package was embedded and there were number of badly designed components such as package parameter parsing. Even now its far from perfect but its better then anything else on Windows.

I don't work for Chocolatey but I am active as community maintainer. I also created AU - framework for automatic updates - which is used on largest community repository. You can see its multiple-per-day output here:

https://gist.github.com/choco-bot/a14b1e5bfaf70839b338eb1ab7...

All the packages marked with download icon are embedded, they contain the software and will work forever. AU also has plugin that publishes them on Github releases also, so even if Chocolatey goes down or not exists any more you will be still able to use them.

Quality of packages there is great, and there are more and more package maintainers that use the guidelines provided.

On the negative side, Chocolatey team behaves toward community repository like it is freak accident of nature rather then major and most important component of the product.