This looks very neat but isn't a PlayIt Live function really.
You can read the number of listeners from a Shoutcast or Icecast server (by scraping the status page if nothing else) and PlayIt Live can generate a text file for each item played and put it somewhere (the "Now Playing" PlugIn does this)..
The two and a variant of your PHP should be able to do what you have shown.
One other feature that although not required, is a HUGE bonus for my sponsors. Radio DJ reads a text file and places the number of listeners from that text file to each item played, and it's logged. It goes into MySQL, and this is a huge selling point as I generate monthly reports of not only when sponsor spots played, but also HOW many times it was heard. They love this. I created a custom PHP program and compiled it to an exe program that reads the number of listeners and dumps this to a text file that RadioDJ uses.
An example is attached. Any idea if PlayIt can do something like this, and log it as seen in my attached image?