I think it's a nice idea.
Supporting Windows users could be a nightmare (especially if you actually don't use Windows at all).
Linux = having everything under your control. If the distro is made with a computer illiterate user in mind, it could be very user friendly, much more than some Windows tools.
My vote goes to SUSE Studio as well, in fact OpenSUSE is the distro I use.
GUI scripting is possible as well (kdialog, zenity, ...).
Imagine giving advice like this:
Boot the latest (put the distro name here) liveCD, click on "Debrick" ("Jailbreak", "Install better PDF reader", "Fix broken display"
) icon and follow the instructions.
Obfuscated script log could be auto-uploaded somewhere (user would need to write down the log ID in case of problems).