I'm not on Windows right now. But the way I hunt such bugs down is usually - logging... lots and lots of logging. I have always a few logging-levels and when the level is set to "debug" then my applications log nearly everything that's done. And I make the logging-level usually a command-line parameter.
Also I had one similar bug once where it crashed only on certain folder-names. Turned out that I had some code checking for special filenames and forgot that in that place the path was part of the filename. So every time the game was in a folder which contained the name "alpha" it did not work anymore (which I did find out when we reached the alpha-release-phase ...).
OMG
I traced it down and found that it was caused by an uninitialised pointer !!!
but I still wonder why it only crashed in that specific folder and not in any others ???
maybe some kind of memory management issue of Windows (maybe solved in sp3) ???