Question
I use iTunes to download your weekly podcast, as well as several other public radio podcasts (Car Talk, Wait Wait, etc), using my home desktop. When I’m on the road (as I am the coming week, when we will be driving down Route 1 from SF to LA), I use iTunes on my laptop to download the podcasts. However, the two computers are not synchronized.

If I haven’t used the laptop in several weeks, I find that I am downloading program episodes that I have already heard when using the desktop. Is there some way to synchronize iTunes on the two computers (the only iTunes feature I use is to download podcasts)? Does iTunes, for example, use a data file that I could copy from the desktop to the laptop just prior to leaving on a trip?

Thanks again for your volunteering to produce Geek Speak.

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Answer
Theoretically, you could synchronize the iTunes Library file, located at
"Macintosh HD / Users / YourUsername / Music / iTunes"

Here are the main problems with that option:
1. If you only synchronize the library file, and not the podcast audio files too, you will likely end up with an iTunes that thinks it has some podcasts, but it really doesn't. That'd be a bummer, to click on a much-awaited podcast on your laptop to find that it's not there. The library file basically points to all the files you have, and stores metadata about them (playcount, rating, etc). If you synchronize the library file without synchronizing the files it points to, iTunes, and consequentially, you, will be sad.
2. If you synchronize the library file AND the music files, and your username at home is different than the username on the laptop, the library file will be pointing to files at "Macintosh HD / Users / YourHOMEUsername / Music / iTunes / iTunes Music", instead of "Macintosh HD / Users / YourLAPTOPUsername / Music / iTunes / iTunes Music"

Here's the solution that I've had work for me in the past. And though it should go without saying, let me just say: Back Up Your WHOLE Music Folder FIRST, including the library file!

After that, here are the steps:

1. Get one computer updated manually -- we're going to synchronize this computer to the other one.

2. (you may have to be sure the names of both of the hard drives are the same -- if you left them named "Macintosh HD," you'll have no problem

3. In iTunes Preferences, Advanced, iTunes Music Folder Location, change it to a path that is not in your home directory. For example, "Macintosh HD / Music"

4. Be sure the "Keep iTunes organized checkbox is checked. (For a screenshot, see the attached file) (When you hit okay, it will probably ask you whether you want to move the music/audio files to the new location. Tell it yes)

5. Repeat steps 3 and 4 in the other computer's iTunes preferences. All of your podcast files should now be located in "Macintosh HD / Music"

6. Copy the library file from the updated computer to the computer that you are updating. This is located at "Macintosh HD / Users / YourUsername / Music / iTunes"

7. Copy the Music folder from the updated computer to the computer that you are updating. This is located at "Macintosh HD / Music"

Now, the computers should be synchronized. Keep in mind though, that if you download podcasts, or otherwise change the iTunes library on BOTH computers, when you synchronize, it will overwrite the library of the computer you are syncing to. So, be careful and make frequent backups. It's not as freaky for you, since you only use it for podcasting, so if you lose some files, theoretically, you can just re-download them.

Also, if you are ambitious, you could write a script to do the synchronization for you. There are even ways to do it with AppleScript, where it will mount the drive over the network for you, use rsync to copy files from one to the other, then unmount the drive when it is done. But with AppleScript, documentation online is a bit sparse. I tried to do this, with some success. I have no idea where those files are now, but if you want to take a look at them, I can try to pull them up for you. It's a fun project -- good luck!

Let us know if this works for you!

Cheers,
Ben