Okay, so I decided to get something started here - no promises since I am a really busy man penguin. Without any further discussion, I present to you "Ask Ubuntu Troubleshooter":
The basic idea is that the application is a simple wizard with dependencies only on the base Qt5 libraries - which are set to be included with the upcoming 13.04 release.
You can find the code for the application here on Launchpad: 
autroubleshooter
So here's where the community comes in:
What information / command output should be included with each of the options in the screenshot above? Feel free to edit this answer and add to the list below:
- Graphics / display driver
lspci
- Wireless connectivity
ifconfig
Feel free to add categories too!