After having done my first experiments I decided to expand on them and see where they took me. At first I decided to merge them together to try to get the idea of excessive typographical information and advertising blending with the forms of the city:

I still thought all the edgy consumerist words together were a bit much. Even so, I like the design of some, so I coloured them to think how I could possibly use them individually or something:

Still not really having any concrete ideas of where to apply them and not quite satisfied with them on their own, I went on to instead work on the illustration of the city more, which I quite liked and thought had potential to become something bigger.
It still looked a lot like a quick sketch (which it was), so I went on to try and make it look more like a finished piece, fixing and organizing the lines and shapes (trying to make the dimensions less random and more calculated, even if the calculations were fairly arbitrary and aesthetic) and developing and adding more stuff throughout as I thought fit. Here’s the before and after:

First sketch of city illustration. 
Final line work of city illustration.
I ended up adding a bunch of elements that I thought would fit and further develop the concept of city architectural forms and graphic advertising blending together. I added some additional elements that weren’t present in the first sketch, some of the themes I had in mind being alarms and sirens, street signs, tunnels, people (loneliness and smallness), open spaces, graffiti, pareidolia, layering, depth and perspective.
Here’s a quick hand drawn sketch I did while working on the illustration:

When adding layering, perspective and depth to the illustration I tried drawing a bit from M.C. Escher’s surreal impossible angles, making buildings and structures blend in forms that make no physical sense.

M.C. Escher – Belvedere (1958) 
M.C. Escher – Waterfall (1961)
This is a screen capture of the illustrator workspace where I did a big part of the experiments, with some that were quickly discarded that I didn’t mention here:

I ended up spending a lot more time perfecting my illustration than I planned on or think I should have. By then I had started thinking different applications and places to put my illustration, as I wanted it to be somewhere other than just my computer and try to avoid it being a passive piece of work that no one would ever see. One of the ideas I had that I liked the most was making it into urban guerrilla projections to project in buildings around the city.