Afterthought
You don't need a special hard drive or anything fancy to do this. Or any outside programs.
It is easy to do through a batch(script)-file using only Windows own utilities - xcopy or robocopy (you only need one little trick to detect when the drive is plugged in)
If you can give me some idea of what you need copied then I can put together a batch-file that will do this nicely for you.
Mac
:-)