Chocolatey has some slightly-awkward-feeling freemium thing going on; there was a good discussion of Windows installer stuff recently: https://news.ycombinator.com/item?id=15791781
Thanks for the heads-up, it's been quite a while since I've needed it.
How has this limited your experience so far? I'm not really well-versed on even the expected impact this has on commonly used applications... is there any?
Well, no one wants a 32-bit web browser, and IrfanView 32-bit cannot handle large files well, I can't remember if the JRE has a 64-bit mode in the free edition but probably not.
In general you will also lose stability and/or performance with complex or intensive applications. For many suites like GIMP, Blender and LibreOffice this is a deal-breaker for me.
https://github.com/lukesampson/scoop/wiki/Chocolatey-Compari... (scoop) is an option focused on dev tools, http://boxstarter.org for repaving dev/vm machines.
Proprietary https://ninite.com for normally-installed stuff, not sure if the free edition updates things.