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I think most people don't actually want a pure random setting. I dislike hearing a song too often and I also like to hear my favorite songs more often, but also not repetitively. So, I have set up 5 playlists that give me what I think is a good mix of my songs. They are as follows:
1: rated 2 and 25 rated by least recently
2: rated 3 and 73 rated by least recently
3: rated 4 and 70 rated by least recently
4: rated 5 and 32 rated by least recently
playlist is any of playlists 1, 2, 3, or 4 with live updating

The numbers (25, 73, 70, and 32) come from multiplying the number of songs in each category by the rating-1, so it is essentially the same as the "play higher rated songs" in PartyShuffle. I leave 1 rated songs for ones that I don't listen to very often. This way, I get a random selection of my music that does not repeat a song until I have more-or-less gone through the rest of them in that rating. And, it generally plays the 5 rated songs about 4 times more than the 1 rated songs.

I found that I do not like the random feature since it often will play one song significantly more than another song. Eventually, it would even out, but in the range of 20 times playing a song, there can be a large discrepancy and I haven't heard some songs in longer than I'd like.

I think the general random setting should randdomly select from a pool of the 20% least recently played songs with live updating. At least, that is how I wish my CD playing in my car worked - I hear the same song played twice in a row about every 10-15 hours of listening.

This guy is talking about 'Party Shuffle' not the straight up 'Shuffle' option.

So of course it has some sort of 'intelligent' (or if you prefer 'stupid') method of shuffle-i-sa-shun...

Also - how much time do these OmniNerds have on their hands?!...

Quevar, thanks for the suggestion. I'll have to set that up, since I've been wanting that sort of a thing. (Now if only iTunes would make playlists tree-able, so I didn't have to have 100's of playlists to scroll through on my iPod).

Come on, Hang on, dont you know how important it is that Quevar not listen to songs he doesn't like a lot too much, and that he hear the ones he does like just the right amount? Any amount of time spent on such fine tuning is VITAL and must be allocated without restriction.

I have 6 playlists used to control how often I hear a song

One star - song rated one star and not played in the last 8 weeks
Two start -song rated two stars and not played in the last 6 weeks
Three stars -s ong rated three stars and not played in the last 4 weeks
Four stars - song rated four stars and not played in the last 3 weeks
Five stars - song rated five stars and not played in the last 2 weeks

Rotation - plays playlists one star, two star to five star

This plays higher rated songs more frequently, and if I need a 5 star fix I can just play the Five star playlist as such.

The playlist that I use most often is this one:

1. Last played in the last 90 days.

2. Not played in the last 3 days.

3. Rating of 3 stars or higher.

I have another one that I also use, which is basically the same, with a fourth rule added:

4. Playcount is less than 10.