smart playlist not working

Do any of the smart playlist criteria involve Podcasts? I seem to recall that causing a problem. If yes, try deleting that criterion and seeing what happens.

Best of luck.

For Live Updating to work, you have to have something that changes in order for a song to be added or removed from a playlist. Things like song rating, playcount, or last played date are "dynamic" elements, i.e. things that change. So in your smart playlist, do you have criteria based on any dynamic elements? If not, then your playlist will not update because nothing has changed.

If your playlist is limited in size, the usual criteria one adds is "Last Played is Not In the Last X Days", where X is any amount of time you want a song to stay out of the playlist before being eligible to come back in. Once a song completes play, it fails this criteria and gets booted out of the playlist, only to be replaced by another song that matches the criteria.

Finally, Live Updating on the iPod is kinda funny. In order for a playlist to Live Update, you have to exit the playlist and start playing something else. Next time you come back into the playlist it will have updated, though sometimes you just need to exit the playlist and come back in for Live Updating to take effect. However, sometimes Live Updating on the iPod simply won't work due to a software bug (the 3.0 OS for Touch/ iPhone is an example). In situations like that you have to re-sync the iPod to get the updating to take place.

I'd just recreate it every time I want to sync

You can update (some) smart playlists by selecting all the songs in it and pressing Delete.
Some won't update, depending on the criteria in the playlist.

Random Should be every time the playlist is accessed.

Okay, but it's not.
Just select all the songs and press Delete. It will refill automatically.

HappyPants wrote:
Why can't my criteria simply be limit size to 14800MB ...
So I guess checking random just selects random songs, it's not actually a criteria. So really that Should be a criteria....Random. Just that.
I Just want a certain number/size of random songs.

You have to have at least one criteria, which can be something as simple as "Bitrate Is Greater Than 1 kbps" which all your music would meet, then set it to select 14800MB selected at random. iTunes will grab 14800MB worth of songs, selected at random, but the contents won't change unless you include criteria that forces songs out of the playlist to be replaced. Otherwise, the playlist contents will never change. Make sense?

HappyPants wrote:
In my case I really don't want to use the criteria as you suggest, "last played is not in the last 'x' days" because sometimes I like to hear the same songs over and over again ... I just can't fit all my music on my ipod and wanted the nano for it's size. So the best solution for me is to just have it randomize my songs a bit every time I sync.

Then how is iTunes supposed to differentiate between the songs you like to hear over and over and other songs that it needs to select "at random"?

HappyPants wrote:
After some thought, I chose to do: last skipped is not in the last 1 day.
That should change quite frequently before putting a song back into the playlist, and it should keep the songs that I like listening to over and over.

Now you're thinking 😉

I still would like there to just be some way of just limiting the size and having it random though.

You can do this (see my first suggestion in this post). However, what you're asking is for iTunes to somehow know what songs you want to keep on your iPod vs. the songs it is supposed to pick at random.

I would recommend you make a regular playlist (not smart) that holds the songs that you always want on your iPod, then a smart playlist that randomly selects from the rest of your music. In the smart playlist, include the criteria "playlist is not (other playlist name)" so that you don't double up on the same songs.

If you want to manage an iPod that is smaller than your library, I would recommend you spend some time reading an excellent paper on how to do this:

http://www.keepandshare.com/doc/view.php?id=1154607&da=y

In my case I really don't want to use the criteria as you suggest, "last played is not in the last 'x' days" because sometimes I like to hear the same songs over and over again.

You can create more than one playlist and sync more than one playlist.
I have a playlist (*My iPod music*) with all songs I want on the iPod.
Then I create a random playlist and mathc rule;
Playlist is not *My iPod music*
Limit to XX MB (the size of my iPod minus the size of My iPod music)