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.
AppSnap is primarily designed for Windows which does not have any decent package manager such as APT and RPM as in the Linux world.
ASCII a stupid question, you get an EBCDIC answer.