Everytime I see something I love start to seek monetization it's something I tend to worry about. Will there still be a free version of that tool? Will they offer something that has enough value that I'm compelled to pull the trigger and jump to the non-free version?
Let me address the question related to Chocolatey and free - I love free tools. I've always loved the Github model, if you are doing things that benefit the community in some way and are open, then it is free. When you need/want privacy, it tends to becomes less about community and thus non-free.
In the same way I think about the model for Chocolatey. We want to always be able to offer a free version and the only way we can ensure that is to have a self-sustaining model. Or to put in a different way, as long as Chocolatey exists, there will be a free version. And the free version will continue to be FOSS (Apache v2 Licensed).