General Game creation help

I would recommend that you plan the whole city out on paper first. Then divide the city into sections and start modelling each section of the city. Milk shape should be well suited to do the job, but you will just have to do enough pre planing on paper for each section of the city. The preplanning will be the most improtant part so work on that and then take the plan for each section of the city and begin modelling in Milkshape. You could probably do something like cutting the city sections by city blocks and then modelling them. Then you could load each section into your blitz program and position them were ever you need to give the impression of a whole city. But that's just how I would do it. There's probably better or similar ways out there. Good luck.