I want to start working on a web map at work to map some of our statistics by city.
I have an idea, but I'm not exactly sure where to start.
Are there any definitive resources that provide step by step guidance on how to do this?
Everything depends on your preferred technology. If you feel at home in JavaScrip, use OpenLayers combined with GeoServer. That should work on all hardware.
If you are better at home in Java, you could look at Geomajas. This allows you to build both front-end and back-end in Java. However, it does not support Bing maps at the moment (it does support Google maps).