rendering OSM data as a military map.

I need to generate some 1:50,000 scale military style maps.

Here is an example: http://www.lib.utexas.edu/maps/ams/italy_50k/txu-pclmaps-oclc-6540719-palermo-249-2.jpg

Here are the basic requirements:

• 1: I do not need anything but static (georeferenced) map image files that I can either print to scale or ingest into a computer mapping system.
• 2: Normal map tiles will not work. The output should be something similar to CADRG (it's going into a system called CPOF)
• 3: I need a large amount of area (20,000 square kilometers) broken into 1600 square kilometer sized chunks.
• 4: I'd like to see topo lines, water, roads and man-made features.
• 5: At 1:50,000, 1 KM = 2 cm. Based on a quick estimate, I'm looking for an accuracy of 1 pixel = 2 meters.

I have downloaded a dataset from OSM. How do I start on this? What software would I use?