iPod ‘how to’ question – any help?

How do you give someone an iPod that is pre-loaded with tunes from the iTunes store: A friend of mine called me last night with this situation: She would like to give someone an iPod and pre-load it with some specific songs she would purchase from the iTunes store.Simple enough. But when I tried to explain to her how to do it, I decided it isn’t as simple as it sounds.

Why this is problematic for a non-technical person: She’s very much a non-technical person and so is the recipient. She wants the music to all be purchased. The DRM “digital rights management” baked into songs purchased on iTunes, along with the skills necessary to connect an iPod to multiple computers (on both the Mac and Windows platform) make this simple-sounding exercise a potential land mine of Christmas morning screw-ups for people who simply want to hit a button and have it play.

After thinking about it a while, this is the alternative I suggested. It’s not a “pre-loaded iPod” but it’s the best I could think of that uses relatively non-technical consumer-level skills. Does anyone have a better hack that a non-technical person could understand? (That’s key: please, no “First, you need to port Linux to the iPod” suggestions.).

1. Give the person the Nano in the box.
2. Using iTunes, create a playlist of the songs you’d like to give, selecting them from the iTunes store (note: you don’t have to purchase a tune to add it to a playlist).
3. In your iTunes window, highlight the playlist you’ve created and then click on the “arrow” at the right of the name.
4. Select the “give this playlist” option and follow the instructions.

To me, this is not really a “solution” to what she wants to do, rather it’s a hack that Apple has packaged as a feature. Nonetheless, if you’re wanting to give someone an iPod and some songs, I think this is probably the way to do it with the least potential for Christmas morning frustration (as long as the recipient has a computer with a broadband connection).

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  • lcreekmo

    Having already lost one computer with my iTunes connection (not the songs mind you, just the connection — songs were all backed up on an external hard drive) and been thru he## and back with iTunes to get properly restored what was already mine — I think you are on the right track with your friend.
    The nice thing is, that while iTunes does have a slight learning curve if you aren’t used to buying online, I think it’s one you can overcome fairly easily. Just don’t ever, ever, ever let your hard drive fail.

  • Hugh

    Be careful gifting a playlist. When I “gifted” a playlist to a friend iTunes gave me an error and said to try later. I tried twice again with the same result only to find that it went through three times. Fortunately my friend only clicked on one of the links and apple credited my account for the other two. BTW to if something similar happens check your itunes music store account to see if the transaction went through.

  • Shannon

    This won’t solve the problem completely, but this service, Rip Digital (http://www.ripdigital.com/howto.htm), converts all your CDs into a digital music library that you can then load onto your ipod. They charge $99 for 100 CDs. Your friend could give a Rip Digital gift certificate and then the recipient could send all his/her CDs off after the holidays. Not instant gratification, but it saves a lot of time. And it’s easy.

  • rex

    I think the “giver” is putting together a very eclectic playlist, so the CD conversion method isn’t right in this case. But it sounds like a great service that would have saved me a lot of time when I was burning all my old CDs a couple years ago.