All the discussion is focusing on comparing it to apt-get. Instead, see it as a useful tool for scripted application installs for Windows.

The main benefits, in my opinion, are:

* Scriptable *

For example, here's a script I've used to build a new Windows dev box: https://gist.github.com/jongalloway/ffc3a8c71dfdab4245bc

* Silent, no-BS installers *

Chocolatey packages are supposed to point to silent, no-nagware, no BS installers (specifying the correct command-line args for silent, lightweight installs if needed). Instead of hunting for the right "Download" button, just find the package on Chocolatey.org, maybe check the release history and comments if you're concerned, and off you go.

* Dependencies *

Since Chocolatey is based on NuGet, dependencies are a first class concept. That means that a tool that requires a specific version of imagemagick (random example) would depend on that version, Chocolatey would ensure that the deps are installed first. That has other impacts, such as making it easy to provide a customized version of an existing application (e.g. https://chocolatey.org/packages/EthanBrown.ConEmuConfig) or allowing you to build a meta-package that rolls up several other packages (e.g. "web dev loadout" or whatever).

If you're looking at Chocolatey, I highly recommend Boxstarter, which takes it to the next level with support for all kinds of things you'd want when automating machine builds on Windows: http://boxstarter.org/