C# :: Multiple Choice Symptom Checker?

I'm doing a project through college which is a diagnostic and support tool for Windows OS's. The application at the moment has a simple expert system which is a Combobox with strings that relate to common PC problems. Then those strings are put through a switch statement and relevant commands are shown to fix the problem i.e. "My printer is not working" will disable all buttons except for printer management, spooler folder etc.

My supervisor who marks my project has said this isnt good enough and wants a more layered hierarchy approach so he's looking for 3-4 groupboxes with tickboxes inside them and users tick the boxes that relate to their problem which will give the functions to support. The only way I can see to do this at the moment is a massive nested switch statement that is really not worth the time. There are 60+ functions in my program so you can imagine how long the switch would be trying to pick and iterate through all of the possible answers.

I'm just trying to figuire out an easier way to do this, rather than a massive switch statement. Something like WebMD which has 4-5 tick boxes and can give out the same answer for different symptoms.

I've attached a Flow Chart I made of the hierarchy Im trying to go for [URL] .....