Are they actual blocks or is each black block an individual building which is how it looks to me? For me it looks unnatural because in a city that dense you're going to get lots of building butted up against each other - they wouldn't all have alleys in between.
What is the large blank spot in the middle of the map? Also, is the city surrounded by walls? If so, you might want to add some suburbs outside of them.
Sorry its taken me a bit to get back to the thread. Thanks everyone for the input, it is greatly appreciated. I think some good questions are also being asked, and perhaps I should have given more explanation at the beginning. Small blocks are what is shown (the smallest square blocks being roughly 100 ft x 100 ft, so you guys have some sense of scale), not building footprints, so this place is pretty expansive for the street and block sizes I have chosen.
The idea I had when drawing this was to take a block/street system similar to what I used for Kessila (in the Nov/Dec Lite Challenge) and expand that urban layout beyond its comfortable limits, mostly to see what could happen. That first attempt was actually quite boring, being a set of nice orthogonal grids covering the whole area. I tried a few more times, incorporating other urban constructs into the mix to add some visual interest. What I am posting is about the fourth attempt, and although I might describe it as that original archaic greek/roman squished into a medievaly-monumental design, it probably does not reflect any real/historical urban fabric at this time.
Moving from this stage to an actual city, I think everyone's comments are relevant and correct. Open space is certainly needed in many areas, and the archaic blocks need to go (or be greatly reduced). Shedding the alleys would still not even push the block sizes into modern day block size dimensions. I agree with THW that providing for those issues should emphasize the existing 'randomness'. In addition, the existing street widths are too small for some areas, but removing the smaller alleys should allow some breathing room for expanding those that remain. At that point I am guessing I will have an almost medievally messy looking city.
The large blank area will eventually be a university (I think I have a diagram in my first post, although it may be difficult to visualize how that translates to what I have done), there will eventually be a campus map. There is also a blank spot where the Temple area will be (which may be a complex of temples in the end). A good suggestion on the suburbs, there is actually one area outside the city walls, Estun, which has not been drawn.
Originally Posted by MrZJunior
I probably won't have time to work on this much in January, but I think I will end up with a fork in the process, moving the section I have already drawn into the 'presentation' phase, and keeping a temporarily dormant copy for the later addition of more blocks (the block-making is relaxing, if time consuming). Some may recall that there is a whole Northern half to this place, and I think it may be more important to get practice in the 'presentation' phase right now than to draw more squares.
Small Update, Big River
I have managed to squeeze out a little bit of time in the last few months to look at this map again, but only really enough to remove a majority of the alleys. The block count has gone from 6000+ blocks to somewhere around 1500 shown here. The blank area will now be the 'upper class' area of the city as well as temple district, and is still being reworked a little bit. The river has been widened some, and Dunfort has become an island. I am toying with idea of a long bridge over the river, but it may instead end up being just the ruins of one, or the city may move to the ocean's edge. The city walls are still being reworked.
As a small bonus, I found an iteration of the university area that I don't really remember ever doing, so I am showing that here. It will probably change as I develop the 'upper class' area.