maybe he meant you can learn a little about the linux environment (if you have never used it before) by using Cygwin...

I am trying to justify it, really I am

As for the update ability on BT2, if you are not aware of this, you should not be entering into a war-game type contest... Even though I don't know many people that dedicate a machine to backtrack, most use it as a liveCD, but to not use the most up-to-date tools is pretty much giving the competition the trophy lol...