If if you got it installed, you next will need a GUI for running ConTeXt, and if some problem arises, you are further away from the solution than ever. :-(
Sorry, you can't use TeX in a decent way if you can't use a shell (AKA command line AKA Terminal AKA DOS box).
Otherwise we get a system where everything is configured "under the hood" by some administrator - and you are in really bad luck if you happen to be your own newborn administrator and read everywhere "if you don't know what to fill in here, go ask your administrator".
Please everyone try to become computer literate! (see also works by Friedrich Kittler)
You took the words out of my mouth; I was going to write in a similar vein. Creating a GUI installer will only give false hopes to the "potentially large base of users." They may be able to install, but will soon run into trouble which can't be solved without a little knowledge of the command line, about paths and configuration files. If you're a billionaire, you could pay a couple dozen programmers to write a GUI for all these settings. But as long as no Mark Shuttleworth pops up, I think it would be better to avoid any misunderstandings. If you're allergic to the command line, TeX is not for you.
Actually, I strongly disagree with the opinion that the only way to properly interact with TeX is via the command line. Counter example: in Mac application development your IDE of choice will almost certainly be Xcode. Although it delegates the entire compilation process to gcc you *never* ever see the command line. And there's no need to. All errors and warnings output by gcc are intercepted and passed on to you via the graphical IDE and you won't lose a tiny bit of information. In fact you gain a lot when trying to track down a problem ... Furthermore, in my humble opinion interaction with TeX should concentrate on programming the actual typesetting language and not on fumbling around with dozens of configuration files ... for instance, if you develop applications you wouldn't want to reconfigure your compiler twice a week either but rather focus on the source code *you* write. Oliver