Well, to be truthful, I love drawing city maps by hand. Or... more like town maps, actually, as cities have far more buildings than I care to draw (I draw each and every building in town).
I start out by consulting my world map, and scanning my subconscious for prior adventures having taken place in that particular town.
Then:
1. I write down major geographical bodies adjacent to the city (rivers, mountains, oceans, deserts, steppes, the like)
2. I write down any locations the PCs have visited, or know of in town.
3. I brainstorm forth any spectacular facilities, strongholds or the like, in town
I start off by drawing the landscape. I use an aerial view, with curve lines for mountains. A) Draw oceans and lakes B) Draw rivers, C) Draw mountains and hills. This is what the settlers had to deal with. Then I draw the major fortifications: Strongholds and city walls. Roads. The buildings of the city itself, markets, spots of interest. Then comes foulburghs and shanty towns.
Reason for being so vocal: I want to find a map and scan it, but I am so darn lazy, it will probably take forever.
Hint 1: Create shades with the flat side of your pencil and use your finger to smear. It will enhance the outcome.
Hint 2: Use wagon wheel tracks for non-paved roads. Detail adds flavour.
Hint 3: Do not rely on computer software other than Photoshop. For geographical maps, fractal edges work nicely, but for city maps the only option is to do everything yourself.
Hmmm... I love maps.
