There isn't an easy way to do this. Some people have experimented with applescripts to simulate a radio station rotation, but the solutions I've seen do not include multiple plays of a single song. They just play more high rated songs than low rated.

Clarification: I did not mean that a song with 5-star rating would play 5 times in a row, just that a song with such rating would play 5 times as often compared to a song with 1-star rating.

If as you said: "radio station rotation solution" that plays "more high rated songs than low rated songs" exists, I would be definitely interested!

Restriction, however: I'm running iTunes on WinXP.

Unfortunately, the solution I was talking about requires AppleScript, which is unavailable on WinXP.

I'm sure someone will come up with a way to manipulate playlists in iTunes on WinXP at some point, but I haven't seen it yet.

Manual playlists allow you to add songs more than once. You could make a smart list for each rating 1-5. Then drag all of the files from the 5 star into a manual list 5 times. Do same 4 times with the 4 star, etc. When you add new music, wipe the manual list and drag again.

Its not a perfect solution but you will have a playlist which will play a higher rated song proportionately more.

That would work, in fact you could create a few smart playlists for each star value and drag the contents into a regular playlist as many times as you'd like.

Hmm, indeed I think this is not a perfect solution, actually I did not want to start using it. Reason: it does not update at all. While adding new songs all the time, and rating (and re-rating) always when traveling (but never when using iPod in home stereo), automatic update is absolutely needed. More suggestions thus welcome!