Ok, just some observations: first, a nice map request.
However, I have to point out that this a HUGE job. Really, really big. This basically screams "vector map" to me. Placing around 10,000 labels on a map takes an immense, utterly immense amount of time if you want them placed well, readable, and so forth. At your scale this is about 60"x50" just for the base map. Which basically means: vectors.
Combining this with a road map style terrain map is pretty hard, because it also involves depicting the terrain - if you want to make the terrain depiction a bit more old-fashioned, that would save whoever you commission a lot of hard work and still give you a decent looking map.
Personally, I would be hard pressed to take on such a large project for 200 dollars - the time/money equation just doesn't hold up for me. A single professionally placed label easily takes me 1 minute or more to get "just right" (which means easily 8000 minutes for 8000 labels, which is roughly 120 hours of work, which is basically 3 work weeks. Just for labels). If someone takes this commission, and they know how to label automatically - I wan't to hear about it and learn how!