I have an older version of Itunes and it does sort by date added. I had to go to Prefernces or something and then enable it - then scroooolllll to the right to see it.

sad to hear about hard drive issues.

before you hook up your IPOD read some more - if the music is all on the IPOD and not the hard drive, the IPOD will try to synch with the nothinginess and you'll lose your music. There are third party apps that allow you to copy music *from* your IPOD to your computer.