A quick and effective way to increase the play counts of any song. No downloads or scripts, works in iTunes version 11.
I'm using Mac, assuming its the same for Windows.
Select song. Play song. Turn Repeat (1) on. Right click. Get Info. Click Options tab.
Change the Start Time to .001 seconds before the Stop Time. Restart song. Press Skip until you reach your desired plays. Right click song. Get Info. Change Start Time back to 0 seconds.