After installing OpenSSL, downloading the pre-built Swig executable, and ensuring the openssl libraries are located in the default c:\\pkg, pip install m2
It's late 2019 and installing M2Crypto is still a pain! After a ton of Googling, finally got it down to the steps below:
pip install wheel
pip install M2CryptoWin32
Using a fresh Python 2.7.17 32bit install on Windows 10. You might need install http://aka.ms/vcpython27 first.
I'd imagine one should use M2CryptoWin64 instead if you've installed 64-bit Python.