How to make a WebMD-esque site

I'm on a high school robotics team (the FIRST Robotics Competition, for those interested), and had the idea to make a site to help out other teams. Basically, teams would input the "symptoms" of what isn't working ("Motor isn't spinning," "LED isn't turning on," etc.) and the site would suggest possibly problems ("The motor isn't plugged in correctly") and how to fix said problems ("Make sure the motor's powerpole connector is plugged into port 0,"). These are obviously basic examples. I've tasked myself with the project, and want to know how I would go about making something like it. I have experience with Java and HTML/CSS, but have no idea what something like this would entail. I'm up for learning any new languages needed, thanks in advance for any help.