I have found an issue with exporting some prop entities with the VMF exporter. I have noticed that many times if I paint props onto a scene (Proxies with Object Paint)... the level will crash CS:GO. I noticed this in the island map I started for CS:S and moved to CS:GO (it worked fine in CS:S but crashes CS:GO). Now I discovered this in my work on Sacrilege where scattering prop details by painting them crashes this map.
I have to experiment more but I am guessing it is something to do with the orientation (rotation) of the props. It may be that the decimal is too long or is otherwise ill-formatted. It could also be that the Object Paint tool paints objects at negative scale... which could be creating an invalid transformation matrix. In any event, I expect to figure it out.