Originally Posted by Ravenas
Great idea... Someone with source modding knowledge needs to get on this!
Its not possible
You can set random spawn points for players, items etc but there is no way you will ever create a random map generator for a Source based game. It would be incredibly resource consuming, and would take an unimaginable amount of time to come up with. There are so many variables to these maps and they absolutely kill a system to render.
I know, its sad