@phpbits - That is pretty cool and I will definitely check out their developer program, but our docs on that kind of stuff is pretty solid and a lot of it is linked to from the relevant dash with inline contextual help already. Benefits of having 90k installs and having to deal with the growing demand for support.
We just released our latest version which was 90% focused on support reduction with built in JS debugging tools (popups use a lot of JS), an in dash KB & support section (via secure iframe) etc.
So I'm not necessarily looking for our users to get help doing setup stuff. We are talking pure troubleshooting, checking browser console for instance for JS errors. The goal being to insert this before our support form can be used. Currently they have to do a doc search as you can see here, before they can submit a new support request, but I want to make that a bit more intuitive and interactive.
As such I would start with something similar to the type used by Microsoft KB like these: http://www.thewindowsclub.com/microsoft-diagnostics-service
Mine would be something like "Select the statement that best describes your problem: My Popups won't open, My popups open on every page, every time I refresh, or don't go away. etc"
Depending on your choice it would take you down a path of tests & solutions. This is no different than what we do in support tickets already, just before they actually get to us.
My goal would actually be able to set it up so that I can pass what options they chose to a Ninja Form or similar to be passed to our support system so we know what they have "supposedly" done already. But that's a pipe dream for now. Putting it on the feature list though .