Can my iPod synch my OTG playlists and give priority to the iPod?

I have playlists that I need to change from week to week and that I need to change on the fly. I create and name on-the-go playlists, but later when I sync my iPod to iTunes, the playlist is no longer what it was. Let me explain myself more clearly.
1. I update an already existing OTG playlist
2. At some point I need to sync to iTunes (much as I dread it).
3. Since my OTG playlist has been around for a while, iTunes wipes out my newer playlist and reverts it to the old stuff that it already had.
I know for a fact that iTunes used to "upsync" my playlists, updating iTunes, but since the latest software update, it's all screwed up.
Is there any way to get it working right? Or do I always need to create a new playlist before I sync to iTunes so it doesn't wipe me out.
Thanks in advance.

Police don't "track down" lost items, per se. They'll keep your information on file in the event that someone finds your iPod and turns it in. Otherwise, there's nothing the police can or will do in regards to finding lost property.
Sorry, but your iPod is most likely gone for good.
Regards.

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I have a couple of steps for you to try in order to get those songs transferred to your iPod touch. First, make sure all of your software is updated with the latest versions. If the songs were downloaded from iTunes, you will also want to delete the songs from your library and then download them again from the list of past purchases on your iTunes account. An article about doing that can be found here:
Downloading past purchases from the App Store, iBookstore, and iTunes Store
http://support.apple.com/kb/ht2519
If you try a sync after those two steps and are still seeing the issue, then I would like you to try syncing the iPod by setting it to manually manage. An article outlining more information on manually managing your iPod sync can be found here:
Managing content manually on iPhone, iPad, and iPod
http://support.apple.com/kb/ht1535
If you are still having issues after that, I have another article that can outline some other reasons why your songs may not transfer to your iPod, and it can be found here:
Some songs in iTunes won't copy to iPod
http://support.apple.com/kb/TS1420
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Can my iPod synch my OTG playlists and give priority to the iPod?

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