Okay, so I've ran some tests to source the problem and here are the results. Each time, I changed something with a simple map to locate where the issues may be coming from.
TDM Map with 15 pre-furnished buildings (Equaling about 30% object memory), a ring of pine trees around the outside, raised mountains around the edges of the map, a large scribble of painted dirt, and 20 or so spawn points (all made to emulate the statistics of my cowboy map): Error Redhorn 80000B
Same map, removed 7 buildings: Error Redhorn 80000B
Re-added those 7 buildings, erased all trees: Error Redhorn 80000B
Previous treeless map, with 7 buildings removed again: Error Redhorn 80000B
Previous treeless and half-buildings map with terrain entirely flattened: MAP UPLOADED - CONFIRMED TERRAIN MAY BE THE PROBLEM
Re-added all trees and buildings, flattened all terrain: MAP UPLOADED
Used the Raise/Lower tool to raise all trees, buildings, and spawn points up atop a 90 degree plateu: MAP UPLOADED
Restored flat shape, used noise tool to create a rough terrain surrounding the edges of the map: Error Redhorn 80000B
Restored flat shape, added 3 simple hills to the terrain: Error Redhorn 80000B
Used smooth tool intensely on all 3 hills to produce rounded shapes: Error Redhorn 80000B
in conclusion, this error has something to do with the terrain complexity of the map. If a map is rough or contains minor differences in elevation, it's not likely to be uploaded. However, a map with near-90 degree angle terrain can still make it through the system fine. So for now, I guess do what you can do with flat maps and we can wait on some kind of patch.
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