Hard drive failed, now I need to re-purchase iTune's library

My father's hard drive failed and now his iTune's library is gone. I have two questions.
1. How can I buy a list of songs from the iTune's music store? I want to avoid re-purchasing individual songs and albums; it will take forever.
2. Is there a valid way to recover the songs that are on his iPod nano? This is only a partrial solution if it can get done.
Thank you in advance for any insight.

If he still has the library on his Nano, hope is not lost. There are programs that will allow you to copy from the iPod. I've heard of Yamipod and iPodRip. You could Google those and give it a try. Not sure if they work on Nano, but I would think so.
Diane Wordsmith

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