Thanks for your comments. I wanted to have the aesthetic be such that it could conceivably be 'handmade' and I did hold back on things like extra texture on the water, which would not make sense if it were drawn. I tried drawing the writing, but it didn't look right. Originally I wanted just one colour, but it was impossible to differentiate the roads.

I am a bit puzzled as to how I will draw things like trees\ vegetation in this style.

Definitely, the copy+paste of some of the buildings does take away from it, but it was a proof of concept as much as anything else.