I found a pretty good way of repeating a section of a song in iTunes, for play along purposes.

(Check out the picture)

I kinda forgot all about this, but I kept manually rewinding back to the part I wanted and it finally dawned on me.

How to:
Right click song>>Get Info>>Options Tab>>Adjust Start/Stop Time

Simple.

Don’t forget to reset it, or else it will continue to play the part specified, when you’re trying to listen to the full song. :)