I’ve been using iTunes for several years and I think I got my first iPod in March 2004, a 20GB 3rd generation model. I have since got a bigger capacity one. But the topic of this post is how I have been using Smart Play Lists.
I have one play list which I use a lot, which I devised so that I don’t listen to the same song again once I have played it on my iPod or on iTunes. It uses the last played date which is recorded when ever you play a track either on the iPod or on iTunes. So this is what my Smart Play List looks like:
So if a track has not been played for more than 10 months and also if it is rated 5 stars it is included in the list. So each time you listen to a track when you next sync with iTunes then that track will disappear off of the play list for at least 10 months in my case.
You can also restrict the size of the list depending on the capacity of your iPod, this adds a bit more variety to each sync.
I also normally turn on shuffle to further randomise the list otherwise you will quickly play all the artists at the beginning of the alphabet and never get to ZZ Top!!
You don’t have to set it to 10 months, you can vary the time span accordingly depending on how recent you want a repeat to be.
I have found this works for me quite well and I rarely get fed up with what iTunes feeds me.
Car keys, house keys, magnifier (my close in eyesight is terrible these days), mobile phone, 
