How Do I make Random Map Generators?
I am a programmer making games and I know that random generation is why 'Diablo' was one of the best games for years after it's release. I just had my artist ask to leave the position and now I AM the crew, lol.

I can draw maps of mediocricy, but I was hoping for advice on how to put the puzzle pieces together to make a map working. I am going to make cities nd I dont want roads leading into buildings and I saw a great example on .
I want to make a ruined city feel.

The most important part of this thread is: Is there any advice for a rookie cartographer on making a randomly assembled map?