While searching for a debug tool equivalent of strace that runs on Windows, I’ve come across Process Monitor. This appears to work well for me. For anyone in search of strace equivalent on Windows, give this one a try.
I’ve also tried StraceNT, but this one was not very reliable as it tends to crash the traced process almost every time.
An equally useful tool for debugging on Windows is DebugView, which captures output from the OutputDebugString calls.