Hey XCali
Its all looking really good.
I like the way you've done the rooftops and left the detail of the buildings nice and clean so we can still see all the details you have drawn on them.
With the labelling its always a matter of taste and personal style, so in a sense we are all experimenting all the time. The thing to do if you don't feel entirely comfortable with the way something has turned out, then try a few different variations (remembering to save each one under a different filename).
With my personal taste I would probably leave the circles around the numbers on the map white or cream, so that they stand out as being separated from the map. They blend rather a lot with it right now, but they are still legible. Its up to you to decide how much you want them to stand out.
With the legend I only have two suggestions. The first is to make number 1 'Entrance to the inner city', rather than just 'to the inner city'. The second is to use a space either side of the hyphen, so that all the lines of the legend have the same format. At the moment you have irregular spacing on those lines with the hyphen sometimes being spaced, and sometimes not.
I hope that helps