Playlists let you organise music in many ways. Rather than listening to an album, you can choose your favourite tracks by one artist, or set up a mix of dozens of artists, all with a few clicks.

Can I copy a playlist and the songs it contains from iTunes to a thumb drive?

If you want to import that playlist into iTunes on another computer, first select all the songs in the playlist, and then drag them to the thumb drive. Next, with the playlist selected in the source list, choose File > Library > Export Playlist. Save this file on the thumb drive.

To import this playlist into iTunes on another computer, connect the thumb drive and then copy the music files into iTunes. Next, choose File > Library > Import Playlist and select the playlist file you exported earlier. The playlist will display in the iTunes source list, with all the songs that you added.

Can I remove the breaks between songs?

The tiny gap between tracks in iTunes can be really frustrating. Try turning on the Crossfade Songs option in iTunes’ Playback preferences. When you select this and choose a time in seconds, iTunes segues tracks, fading from one to the next.

If you have specific songs with portions of silence in the tracks themselves, you can alter the start and stop times within the Get Info window’s Options tab, or use an external audio editor to alter the tracks permanently.

Is there any way to associate a single song file with multiple albums?

You can’t tag one song with multiple album tags. But if you created playlists for each of your albums, you could add one version of a song to each playlist. The album name attached to the file would be the same each time, but it would appear in the playlist as though it were from the album for which you created the playlist. But keep in mind that the track number will be whatever it is for the master file, so albums might not play in the correct order.

Can I combine several ‘favourites’ playlists so they play together in iTunes?

There are two ways to do this. The first is to drag the playlists you want to listen to on to the iTunes DJ icon in the source list; this adds their tracks to iTunes DJ.

Another way is to create a smart playlist that contains those multiple playlists. Choose File > New Smart Playlist. In the resulting window, choose Playlist from the first pop-up menu, Is from the second, and the name of one of your desired playlists from the third. Click on the plus-sign button (+) to the right of that line and do the same thing again, adding a different playlist. Repeat until you’ve added all the playlists you want. Before you click OK to save the smart playlist, make sure to select Match Any Of The Following Rules at the top of the window. Save the smart playlist, which will contain all the songs in the selected playlists.

If you use the Crossfade Songs option, you can choose the overlap time for tracks

I listen to a lot of plays as audiobooks. Is there a way to combine many small tracks into one so there are fewer tracks?

I have recordings of all of Shakespeare’s plays in my iTunes library. The easiest thing in this case is to create a smart playlist: for example, Artist Is William Shakespeare, Album Is The Tempest, and Plays Is 0. As you play each track, it gets removed from the playlist, since the play count increases to 1.

Note that you need to change the files’ media kind to Music (select the files, press Cmd-I, and then click the Options tab and choose the Media Kind menu).