iTunes doesn’t make it easy to build playlists with multiple iterations of the same track. You can do it; but with every addition iTunes puts up a dialog box and asks you if you indeed intent to do it. It’s an annoyance.
I wrote a short AppleScript that allows you to build a playlist built with multiple iterations of a group of selected tracks. The script allows you to specify the name of the playlist and how the tracks are to be added (all of the iterations of one track back-to-back [AAABBBCCC] or repetitions of each group of tracks. [ABCABCABC]) Read more after the break.
We use this to build Suzuki listening playlists.