can confirm; this seems to occur because the windows in both cases are part of a "func_detail" thing which means things don't render in the right order. we'd make a fix of it if we knew how to get the map to actually compile on our machine :/

so, hacky semi-fix: use Map Retexturizer to set those to zero opacity. It does mean the windows are entirely transparent without a texture, and props still clip in front of any decals on them, but it's better than the alternative, and it's how we'll be fixing it on our server using this map.