Admittedly I never though about prisoners doing any of those things, including D&D, but hey, whatever works.
Just try to tell the death row inmates your monster rolled a 20
Package Management for grownups
Additionally, what if MS decides to change the way programs are allowed to behave yet again? (I'm not saying this is necessarily a bad thing) Are you sure your package management solution will still be working? I couldn't care less if the manufacturer is Microsoft, Apple, a community project or satan, I just want to be sure that it will work in a predictable and integrated fashion for a lot of time. Windows, with its proprietary format and dependence on the capabilities and priorities of a SINGLE company doesn't really offer that.
Remember Darwin; building a better mousetrap merely results in smarter mice.