Sync play count, last played, and rating with iOS 5
From other threads (https://discussions.apple.com/thread/2717423?answerId=16563011022#16563011022 and https://discussions.apple.com/thread/3408222?answerId=16505730022#16505730022 for example) it is clear that there are some problems with play count, last played, and rating information updating and syncing under iOS 5. I have at least a partial solution. I am posting it here instead of under one of the existing threads because 1) some discussions seem to be confusing the difference between updating the iOS 5 device data and syncing the updated data to the computer, and 2) some of the discussions are focused iPhone, and though the problem appears similar I only have an iPod touch to test the solution on.
First of all, this is not a new problem. Prior to iOS 5, I would plug my iPod Touch into the computer and not see any play count or last played data for songs I knew I had just listened to. I discovered that if I clicked (in my computer's iTunes display of the iPod) on one song that I had recently listened to, it would suddenly display play count and last played for all the songs played since the last update. I could then transfer this playlist data (more on this in a minute) to the corresponding songs on the computer. Under iOS 5, this no longer works, and in fact causes the new play count and last played data on the iPod to be lost. However, under iOS 5 there is a way to get this information to update, even though you don't see it when you first connect to the computer.
To make this work, you have your iPod set on Manually manage music and videos under the Summary tab of the iPod settings in iTunes. I have messed around with this for hours, including several restores and resets of my iPod touch, and have found no way to get this to work under various Sync Music options. I have been using the Manually manage mode for years because I use my iPod with numerous different iTunes Libraries on several different external hard drives.
Here's the trick: Manually manage must be in effect before you connect the iPod to the computer. After your iPod shows up in the iTunes interface on your computer, in the main view (where it shows the different tabs at the top and capacity at the bottom) there is a Sync button at the very bottom right. Click on this and wait for it to go through the Sync steps (don't worry, you're not losing anything), and, voila, when you go to the songs (on the iPod) you have listened to since the last time you connected to the computer, the play count and last played data will be there.
Unfortunately, it's not a simple matter to get this data synced to the computer, but it can be done. At first I thought that once I got the data to show up on the iPod I could go to the Music tab and Sync Music to get the playlist data to the computer, but this does not work. It will sync the play count and last played data that are on the computer to the iPod, overriding the newer data. The way I have been getting my playlist data from my iPod to my computer without ever changing the Manually manage setting is by using the Copy Tag Info Tracks To Tracks script from Doug's AppleScripts for iTunes <http://dougscripts.com/itunes/scripts/ss.php?sp=copytinforackstotracks>. This isn't hard to download or install or use and copies playlist information very quickly.
I have never had a problem with play count or last played on my 2nd generation nano, which still works beautifully. As far as I can tell, play count and last played have never worked well on the iPod touch; there are threads in discussions complaining about this from years ago. It would be nice if Apple would recognize that these are extremely important features to many users and make it a priority to make these basics work before (or while) adding a lot of other fancy features.