Chocolatey is attempting to be an package manager for Windows. Like apt and yum. I love the idea. The execution thus far has been fairly disappointing. I would love to be able to issue a single update to upgrade the tools I use. Unfortunately this isn't always so easy with Chocolately.
The main problems is a lot of abandoned packages and simply not being as reliable as Apt. Maybe the one impressive thing is that is seems to play nicer with applications installed outside of the package manager, not great, but less terrible. So tools that auto-update might cause problems. And you probably want to keep track of software you are managing a package with Chocolately or not. Which can be even more annoying.
The abandoned and out-of-date packages is not really a problem with the tool itself, but the management and cultivation of packages and people to maintain them. You can't solve the problem of volunteers, but it would be nice if there was a review process which tagged packages that were out of date. It could also use some improvement to how it interacts with software installed outside of Chocolatey.
I'm starting to get into .NET development and windows server management. I'd love to have the simplicity of a command line based package-manager for implementing automation and DevOps practices. If not Chocolatey I hope MS will create or endorse and improve a similar tool.
