[bobbyd2000]

So I'm sure many iPhone users have the same problem I do. That is, you have way more music in iTunes than the iPhone will hold.

I want to set up some kind of Smart Playlist(s) that can constantly update and randomize so that everytime I sync my iPhone, I get a different selection of music, without having to do so manually.

I've tried using Smart Playlists limited to a particular amount of GB, but they don't randomize.

Apologies if this has been discussed elsewhere on the forum.

Any thoughts would be greatly appreciated...

[abalboa3]

I am also very interested in this. I am going to be changing from 32GB Touch to a 16GB iPhone. I'm definitely gonna need a good way to keep my fav music on it with room for apps, pics, and videos.

[HymerSchmidt]

I'm not sure this functionality exists. You might be able to do a party shuffle and paste the selections into your sync playlist. But if the functionality did exist, it'd be where you set your syncing preferences, and I don't remember seeing anything like this.