> 2) We have to remember to do this change every time we upgrade to a 
> newer version of Python. 

Every new MSVC release brings new problems, as far back as I remember.
Did you actually try to turn it off? Did it work? What if you do
'open("foo","bar")'? IIRC, turning this CRT checking code back on,
regular Python code can now crash Python, by triggering a CRT
assertion (these assertions are stupid, in the sense that they ban
behavior that is completely conforming to the ISO C standard, and
consider it incorrect). Turning off the assertions is the only
supported way to override the CRT behavior to crash the application.

I don't quite understand why this all affects your code. Are you
using ASSERT() by any chance? If so, why are you not using assert()
instead? That doesn't go through CrtDebugReport, AFAICT.