How to outsource the updating of my iPod's music library?

Adding to your iTunes Library is easy. Just go to the File menu and select "Add to Library..."



From there you'll want to select the media files you want to add to your iTunes Library and click "Open". iTunes will then copy the files to its internal storage and add them to your list.

To change the location iTunes stores its files, you can select the Advanced tab under iTunes-->Preferences...

Thanks for your answer, but unfortunately your answer brings up a bunch of new questions.

I suspect that in the end I'll need some sort of write up. I'll go ahead and ask my follow up questions, and if they're too detailed perhaps you could point me to a more complete asnwer?

Follow ups:

- It's not clear from your answer who would do what and when? What does the outsourcer do? Does the outsourcer need to have itunes? What if the outsourcer has her own, separate iTunes library?

I guess it makes sense that if the outsourcer has done her job correctly, and hands me back my external drive with a bunch of new stuff added to my library, that my version of itunes will automatically know how to recognize the new AND the old content AND know how to re-synch my iPod. Is that much correct?

Thanks!

Hi:
Two things that I thought about:
1) Is the iTunes folder on your external drive? Adding music to that drive without your copy of iTunes on that drive will not update your library.
2) Why are you thinking about giving an external drive full of thousands of dollars of music (and the hard work to compile it all) to a perfect stranger or even a friend? That is a bit of a risk. Perhaps a better solution is to use another harddrive for the ripping, attach the drive to your laptop, and then add them into the library using the method previously described. If you don't mind the mp3 format, the worker bee doesn't even have to have iTunes. They can use something else.
As for who could do it, I suppose anyone with the time, really.

If you want to offload the digitization of your collection to a third party, all they have to do is deliver a drive with your media encoded in the desired format. From there you'll import them into your iTunes Library. iTunes will make a copy of the file and add it to the list. It's up to you to create playlists, etc., unless you want the third party to also do that for you. If that's the case, all the third party has to do is export the play lists into your favorite format. On your end, you just replace the base path with your iTunes Library path and import the file. The play lists are plain text files.

The easiest thing for a third party to do would be to use a new drive formatted for your target system and switch their iTunes Library to point to it. They'd rip using your preferred encoding method of choice (AAC works for me) and export play lists to it. Remember to keep it clear that digitizing and organizing your music collection are two different functions. The digitization process will naturally keep tracks together with an album (LP, CD, or other) and iTunes will add genre and other metadata, so you won't have to worry about that stuff. What it won't do is create personal play lists. That's up to you. Or you can leave it up to iTunes Genius and be pleasantly surprised.

Also, keep in mind that you're handing over your media to a third party. Make sure they're going to respect your old albums and CDs. The rule of thumb is that if you're the kind of person that hesitates at letting your friend borrow an LP, then you're probably better off digitizing it yourself or finding a copy online.