In this universe these games are closed source and there's no guarantee that, if someone for example uses them for training to crash airliners, a red flag isn't raised somewhere.
the number of red flags thrown would be excessive. Who hasn't purposely crashed their plane in a flight simulator just to see what happens.
Or to see how difficult it is, which is not difficult at all. Hitting the ground of course is trivial, but you can probably hit a skyscraper the first time you boot up a flight sim. It's hard to imagine anyone doing much "training" specifically for that.
I reserve the right to crash virtual planes into virtual buildings, I dont know what else youd use a flight simulator for.
Given that this is Microsoft i would be very surprised by this. They are too incompetent to be able go think about such a huge details. And even if they were forced to implement this feature it would be poorly done and would probably have a lot of false positives which would make the data almost useless. (I dont know about games from other companies)
I think just about every kid who has played a flight sim has intentionally crashed into a building at least once.
One example: the release of Propeller Arena for Sega Dreamcast was scheduled for September 19, 2001. The release was canceled just days after the attack.