I recently answered a lot of questions about iTunes in other forums, and those answers are reproduced here so that others can benefit. They are segmented into sections on file management, transferring to or from devices, iTunes Store accounts, iTunes playlists, and iTunes performance.

You can learn more about iTunes in the most recent edition of my book iPod and iTunes For Dummies

File Management in iTunes

• “What is the best way to manage music files, i.e. backing them up, with iTunes?”

The best way to manage your iTunes library is to use Apple’s Time Machine (with Time Capsule) — you did ask for the “best” way. You don’t have to worry about it. Your Time Capsule always has a backup. You can then use iTunes Match to copy most (though not all) of your music to iCloud, for a second backup. That’s basically what I do.

• “How does iTunes keep track of its music library?”

Songs ripped or downloaded are copied to the iTunes Media folder — unless you uncheck the “Copy files to iTunes Media folder when adding to the library” option under the Advanced tab in Preferences. So normally, iTunes makes a copy of the music file, and stores it in the iTunes Media folder. If you delete the original file, the copy still exists in the iTunes Media folder.

If you uncheck the “Copy files to iTunes Media folder when adding to the library” option, iTunes doesn’t make copies of the files, and instead points to the original files. If you delete the original file, it’s gone. iTunes may display it, but won’t be able to find it — you’ll see an exclamation point next to it in your iTunes library.

• “Some of my stored CDs are fragmented i.e. if an artist has recorded with another artist then the track is stored separately and not in the overall CD. How can I consolidate separated tracks so they are included where they should be?”

The filename and location within artist and album folders change when you change the information for a song in the information fields. For example, if you change the song title, the filename also changes. If you change the artist name, the folder name for the artist might change or the file might move to a new folder by that name.

If you want a compilation album to be stored within an artist folder, you could change the Artist field. You could, for example, create a new artist “name” that combines two artists (Paul Simon and Art Garfunkel, for example) and use that name for the albums, to store it in the “Paul Simon and Art Garfunkel” folder.

On the other hand, if you just want the songs/albums to sort in the list as if they were by the same artist, you can change the Sort Artist field for the artist under the Sorting tab in the Get Info window. You can add the artist name the way you want it to be sorted, as I do with “Hartford, John” in the Sort Artist field, so that John Hartford songs show up in the H artists (as if the artist is “Hartford, John”) rather than in the J artists when sorted alphabetically, but the artist name still appears as “John Hartford.”

You may want to change the Album Artist field under the Info tab in in the Get Info window and the Sort Album Artist field under the Sorting tab in the Get Info window, or fill them in if they’re blank, for certain songs on compilation albums or music from box sets. iTunes offers both Artist and Album Artist fields for a song so that you can include the album artist name if it’s different — such as the artist name for a compilation album that features songs by different artists (for example, a duet album by an artist who brings in other guest artists). This is a sorting trick, not a way to reorganize the way the files are stored.

Transfer to or from Devices

• “Tony, this may be too basic a question, but here goes: Would tips cover how to transfer the data on my iTouch 4 to my new iTouch 5? (OK, you guessed it; I’m near 70.)”

If you first synchronized your iTouch 4 music, videos, apps, and other content with your iTunes library, and your contacts, calendars, bookmarks etc. with iCloud (or using iTunes with your browser, desktop contacts, and calendars applications), and your photos with iPhoto or a photo folder, you can simply synchronize your iTouch 5 to the same iTunes library for content, and iCloud (or your desktop applications through iTunes) for your contacts etc., and iPhoto or photo folder (through iTunes) for photos.

If that’s not an option for some reason, most alternative solutions will copy your music, videos, podcasts and some data (contacts, calendars) to your computer (either to an iTunes library or just the files). You can then use iTunes to synch them with your iTouch 5. You can find these utilities at the bottom of this article: “Tips on Using iPod and iPhone Models“.

• “Your book refers to Tip #3 on your website for moving files from an iPad to iTunes with 3rd party software. I cannot find it.”

My apologies. Somehow it was left off the end of the “Tips on Using iPod and iPhone Models” page. You can find it at the end of that page under “Using Utilities to Copy Files and Music”. Thanks!

iTunes Store

• “How do I get rid of this error on iTunes: ‘This Apple id has not yet been used with the iTunes store. Please review your account information.’?”

You should log into the iTunes Store (click iTunes Store button in the top right corner), and click Account in the Quick Links section on the right side of the page. The Account Information should appear (you may have type your password first). If there is a problem, it would be listed there.

• “What happens to the songs I’ve already bought if I change my region settings in iTunes?”

Your purchases won’t vanish, but you won’t be able to buy in both regions at the same time. To do that you would need to create a separate account for each region.

• “What was the first song ever downloaded from iTunes?”

I couldn’t find the very first song downloaded. The day iTunes Store opened in 2003, the top seller was “Stuck in a Moment” by U2, and the top album “Sea Change” by Beck. (My first download was the exclusive iTunes offering “Diamond Joe” by Bob Dylan.) More than a million songs sold in the first week, which is amazing considering only Mac users could purchase them.

 iTunes Playlists

• “How do I create a Smart Playlist that includes videos I have started watching but have not finished?”

This is almost a trick question, because you can’t really do it in iTunes exactly as you want it. However, these instructions get you closer to what you want (i.e. “You can’t always get what you want / but if you try sometimes / well you might find / you get what you need”).

When creating or editing a Smart Playlist…

Create the first condition by choosing from the pop-up menus:

1. Media Kind, is, and TV Show (“Media Kind is TV Show”). The Match pop-up menu appears. Choose to Match All from the pop-up menu. Then create the second condition:
2. Plays, is, 0 (“Plays is zero”). The Plays measure is a play count. You have to play the last moment of the show, i.e., all the way to the end of the credits, for it to count as being played. So any TV shows you’ve already started will show up on the list, but unfortunately mixed in with unplayed shows. You can then add a third condition, such as:
3. Date Added, in the last, 4, months (“Date Added in the last 4 months”) to get only the most recently added shows.

However, I prefer stopping at 2 conditions, and then adding the Date Added column and sorting the playlist by clicking the column heading Date Added, so that the most recent rise to the top.

You have to create separate Smart Playlists for TV Shows and Movies — change TV Show to Movie in the Media Kind condition above.

Comment on the answer:
“Thanks. I already do something like that. But I’m running my own DVR, so I have a host of recently added, unwatched content. So this works for browsing the smart playlist within iTunes, but it doesn’t work for syncing my recent shows I started watching to my iPhone.”

• “How can you open multiple playlists in iTunes v11?”

Apple removed that feature. You can duplicate a playlist and then edit it, and you can use the Add To button under the Playlists tab to add albums and songs (but not playlists) to a playlist. That’s about it.

iTunes Performance

• “What does iTunes do when it says ‘Determining Gapless Playback Information’?”

Albums on CD, or downloaded albums, that are “gapless” (no gaps between songs) are detected by iTunes so that they play properly. Gapless playback is always on unless you turn on the Crossfade Songs option under the Playback tab in Preferences.

• “How can I cut down on the amount of memory iTunes uses on Mac OS X?”

Mac OS X has very efficient memory management that automatically allocates memory and adjusts the contents of memory as needed. You don’t have obvious control over it. iTunes when first opened doesn’t use as much RAM at first, but uses more as it plays more songs and especially long playlists. The only way to reduce its memory footprint is to quit and then reopen.