The UI is clean and easy to use, self-explanatory enough that it doesn't need instructions. It really cleaned up the download game and makes it fun and simple to search for programs to download. Makes it easy to locate and manage new programs easily.

Awesome experience using a product that makes it easy to install a various range of tools

Chocolatey offers version control for our env as well as a simplification of deploying software to non-admin users. It provides a well developed GUI interface for users and a solid cmd line for more technical users. One of the better things it offers is powershell scripting, you can follow the chocolatey rules, or just use it to deploy a powershell script when needed. It has a stdlib which has it's own functions, or you can write your own - which my org has. We use chocolatey for mass deployment and version control in my company. The developers have/are introducing a reporting and central control console, but it's in beta/early intro and while our company will pick it up eventually, we use pdq inventory for the moment for reporting details. The support staff are top-notch and really know what they are doing. It can be difficult to understand some of the documentation as it is very technical. I've never had a problem with support breaking down the concepts for me when I don't understand them. There is a free version, and a paid-for Enterprise version. I dont know anything about the free version, but the enterprise version includes a background service. This service will essentially hide everything from the user. While your applications need to be packaged well, and not say leaving a prompt hanging out there waiting for input, any windows/etc that could mess with install are hidden. Yes, sometimes silent installs will suppress these, sometimes applications aren't written that well however and chocolatey covers you in that case. There are growing pains with the product as they support new interfaces being developed, support has never let me down however. There will always be the occasional quirk, and there are definately some bugs in certain packages, however with powershell there is a variety of ways things can be re-tried. The support staff works through issues we have and works closely with developers. It is not uncommon for your particular issue to be worked into a new update once identified fairly quickly, and if there isn't a release soon they do have beta offerings. While I can't comment on the free version of chocolatey as I simply dont have knowledge of it, I can fully recommend the enterprise product. Make sure you invest significant time to training your application packagers to learning it, and perhaps working with the support staff and it will pay off very well for you. While it certainly isn't something you just click-through and your up and running in a few minutes, if you have a complex environment it can help simplify for your users.