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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...
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As I said, you can update the tools while it's running as a LiveCD only. You'll just have to do it again next time you run it.
