1) install cygwin from cygwin.com make sure that you check to install gcc, cc, stdlib, openssl, etc, default installation will work.
2) download pyrit source (svn checkout http://pyrit.googlecode.com/svn/trunk/ pyrit)
3) modify ./pyrit/cpyrit/setup.py adding a reference to lib crypto
libraries = ['ssl','crypto']
4) ./setup.py build
5) ./setup.py install
6) ./pyrit.py benchmark
If you have any problem please let me know.
vf
PS: I don't have tried with cuda ('cause I've an ATI), but if someone can give me a remote desktop or logmein or ... I would try