Fair enough for legacy maps, there is a great deal of work.
By obstructions you mean solid objects that prevent vehicles to go across, like a house placed on top of road, right?
I have not dived in DCG but it does not look different from what map building is, text files you can edit and XY coordinates similar to those you have in any FMB mission file. Certainly something that can be processed either using database queries or a bash script under Linux (my preference ...).
All objects placed on a map having coordinates, it would be fun to have clash detection to get all these entries that are in the way deleted ... (add Dr.Evil laugh !).
Back to virtual reality, this road going down to Porog, Lyubytinsky District you see below is done manually (bends, straight bits and so on):
Seems smart to use the coordinates of the objects constituting the road instead of manually placing a vehicle to pick the data you are after. The classic IL-2 zig-zag roads also have their entries stored (although I am less familiar with them, not to my taste!).
As for what you need to learn for map
making data handling, actors.static manipulation is probably all you are after.
In
this tread Uzin posted a link to a tutorial
https://www.mediafire.com/download/jk32ohj01yp0e6h/Actors_Tutorial.rarI am looking at the moment at using Geo-positioning for generating the names of cities (instead of doing them by hand), what a great deal of fun this hackable game is!