Hello, I entered a competition for a logo design MyCity, and I decided to make a tut how to make a great looking simple logo.
Finished Result will look like this:

Let's start...
1. First you need to create a new Transparent 500x500 layer (File/New).
note: It would be easier if you turn on rulers (View/Rulers).
2. Create elypse with elypse tool. Start making elypse from 2x2 (with Shift button), and finish about 16. As on picture.

3. Make again elypse but you need to select Subtract from shape area
. Start making from aprox. 3.4.
4. Then in layers tab, on "Shape 1" right click and Rasterize Layer.

5. With Brush Tool
, paint some lines as edges of buildings...
6. Fill up empty space with Paint Bucket Tool, and again repair empty space with Brush Tool. You would have something like this.

7. But edges are not precious and nice. We need to select Rectangular Marquee Tool
, and slowly selecting areas about buildings. If you want to select all in just one step, you need to press Shift button while selecting. After you select, press del button on your keyboard.
8. This part is over. When you all finish with painting and deleteing, you can rename layer to eg. "Town Form", and you need to enable some effects (right click on layer, and select Blending Options).




9. With Rectangle Tool make a windows. I choose to create 29 windows. And later you can group them in to smart object. Also you can create new grup
and rename it to e.g Windows, as I was.

10. Now select Magic Wand Tool, and check all three option boxes (Anti-Alias, Contiguous and Sample All Layers). Hide all windows what you painted, and select Town Form layer, and click on this object.

11. Now it's time to select color of your logo, or with Gradient Tool make a fade effect. After that deselect and unhide windows.

12. Create text with Horizontal Type Tool and type a company name. I used MinionPro fonts/BoldCn.
13. Add some effect (right click on layers).






14. Your logo is finished!

PSD File is available :: Here ::