Your two questions are closely intertwined. So, one at a time.
You cannot see the total playing time for a Playlist on the iPod, but you can in iTunes. If you select the Playlist in your iTunes Library, at the bottom of the window you will see: 11 songs, 1.5 hours, 111.1MB for example. If you click on that text, the information will change to: 11 songs, 1:34:12 total time, 111.1MB which is probably more useful to you. Then (because you need that information on the iPod), I rename the Playlist so that it contains the playing time information. So in my example, it became Another Chill - 11 @ 1h34.
I realise that you are making these Playlists on the iPod, but that my solution only works after that Playlist has been shown in iTunes. This brings us to the other problem. (You're lucky, in my case, every single Playlist on my iPod Touch was deleted from both the iPod and iTunes. And I mean every Playlist, including the standard ones created by iTunes, such as the Recently Added one.)
There is an ongoing problem that means that Playlists created on an iPod are now not added to the iTunes Library (as they should be), and they are deleted from the iPod as well, whenever the iPod is Synced with iTunes. I have reported this, as a bug in iTunes, several times. There have been three or four iTunes updates since my first report and the problem is yet to be fixed. Incredibly, the last update (iTunes 10.6.1.7) has partially fixed the issue. A playlist created on an iPod Classic is now added to iTunes, but so is an empty Playlist along with it. The problem remains as before on the iPod Touch, Playlists are deleted from the Touch.
So I've sent in another bug report.
In the meantime, all you can do is:
- before Syncing the Touch, create the same Playlist in iTunes that you previously created on the Touch.
- once you have created it, you can see the total playing time as I indicated above.
- rename the Playlist so that the Playing time is now is the Playlist name
- Sync the iPod. The Playlist created on the iPod will be deleted, but the Playlist you created in iTunes, complete with the running time, will now be added to your iPod.
When this bug is eventually fixed, there will be a slight change in what you need to do:
- Sync the iPod to iTunes. The Playists created on the iPod will now be in the iTunes Library. (Do not remove the iPod.)
- rename the Playlists so that they have all the information you require in the title
- look on the Device/Summary pane (tab) and click on Sync. The revised Playlist titles will now be on the iPod.
In the meantime, if you feel like adding your weight to my bug reports, go to http://www.apple.com/feedback/itunesapp.html and under I have feedback about, select other, since there is no longer an option for "bug report" in iTunes.
I realise that my suggestion involves some effort, but if it gives you the information you require, then hopefully, it should be worth it.
