Clint Waggoner1 (an old boss) once told me, "If you wait just a little bit longer, things tend to resolve themselves." After saying WMS is OBE and baiting people with the #WMSisdead hashtag on Twitter, I felt that I should prove my point by using the tools I mentioned and documenting the process to create custom tiles and display them on the web.
Project deadlines, a long weekend at the beach, telecons, and a cruise to Cozumel :) resulted in putting it off. As usual Clint was right.
The Chicago Tribune published a five part series on how to make custom maps using PostGIS, TileMill, Mapnik and display it on Google maps. Their code is also available on github.
1I have undying respect for Clint because he used to dynamically allocate memory by wiring magnetic-core memory as his program was running. He did this on a PDP11. In a sub. Next to a nuclear reactor.