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ArmA 1 aka Armed Assault (ArmA)
Here's how I would start:
Create a high-resolution composite image sat map of the area from Google Earth, making sure 1 pixel = 1 meter.
Create a heightmap from DEM to match the sat map. Do some erosion and the like.
Create basic mask file and ground textures.
Import into Visitor and create a .PEW file.
Clean up the coastline - always a problem getting that neat.
Using the sat map, create a background image for street and building placement reference.
Do roads.
Do buildings and other objects.
Create new sat map for in-game using heavily edited original Google Earth image as a starting point.
Refine mask file.
Creating the hi-res sat map from Google Earth is the initial time eater. Use Google Earth Image Downloader which automated the process, few such utilities are available.