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Weighted play by ratings is absolutely the key to making your iPod a true personal radio station.
This is also not a perfect solution, but here's what I do:
Create the following smart playlists:
5 star songs that have not been played in the
last 7 days
4 star songs that have not been played in the
last month
3 star songs not played in the last 90 days
2 stars not played in 6 months
1 star songs not played in a year
Finally, I have what I call a weighted random playlist of songs that are in any of those 5 smartplaylists.
It's taken a while for me to figure out the right length between plays to set for the different ratings, but I think what I've described above is working pretty well.
The problem with this system is that automatic update doesn't work for playlists that reference other playlists on the iPod. It works in iTunes, so I would hope this is a bug they'll eventually fix on the iPod.
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Thanks - - this is helpful. I've found another way to use iPod as a personal radio station. Have a number of playlists with varied types of music (2 stars; Absolute Favs; Never heard; etc.).
As you know, you can create an On-The-Go playlist to capture several iPod playlists. I do this to mix different types of music.
If I want to give added weight to a particular playlist, I highlight it twice for the On-the-Go playlist. Doubles the possibility that one of its songs will be heard, and I've rarely (if ever) run across a repeat song this way. . . .