I am getting random crashes on my C++ application, it may not crash for a month, and then crash 10 times in a hour, and sometimes it may crash on launch, while sometimes it may
Two more pointers/ideas (besides core dump and valgrind on Linux):
1) Try Nokia's "Qt Creator". It supports mingw and can act as post-mortem debugger.
2) If it's feasible, maybe just run the application in in gdb constantly?