Hi KungFuSquirrel,
yep, had the idea of making that "skyline" in my january vacations to Salzburg in Austria (took pictures from an elevated position to catch the church towers, domes etc.).
The visibility... well yeah, you can see a lot of it from the player's POV, but like in a real city it depends on where you are 
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In a few places you won't see much of the skyline due to buildings on your left and right, but I made most streets end with mid-height buildings to open the view a bit. The main purpose was to keep the illusion of a big city feeling alive for players using the secondary routes across the railway tracks (middle picture) or through the upper storeys of the buildings.
Edit:
[Blocked Image: http://www.albatros44.de/soviets/sovc9k.jpg]
[Blocked Image: http://www.albatros44.de/soviets/sovc10k.jpg]
[Blocked Image: http://www.albatros44.de/soviets/sovc11k.jpg]
(connection point of ropes messed up in last screenshot)
).
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, I've spent many months on the road just to get references of buildings from about 1870 to 1930. I'm certain there have been plenty of places that featured this kind of architecture a long time before the 1920s.
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