How can I prevent songs from being duplicated when adding them to my iPod?

One feature I really like about iTunes is that if you have a song on a playlist, iTunes will notify you if you are adding a duplicate song to that playlist. I am looking for the same help managing my iPod.
For example if I have a playlist in iTunes called "AAA" and a corresponding playlist on my iPod called "AAA", my aim is to have the same content on each. If it is a playlist that I update/change on an ongoing basis on my iTunes, my issue is that I have to remember what songs I have updated or deleted off of this playlist in order to avoid duplicated songs when I have my iPod plugged in.
I would like to just drag this "AAA" playlist from iTunes to my iPod and have just the new songs be added to the "AAA" playlist on my iPod.
Hopefully there something I'm overlooking and therefore a way to constrict what is added to the iPod. If you know how to do this, please let me know because this would make iPod music management just as great as iTunes management.
THANKS!

I turned off "manually manage music and videos" years ago and sync my iPods by syncing "selected playlists". Any playlist changes I make on the Mac are automatically synced to the iPods when connected.
Watch this video for suggestions: http://www.apple.com/itunes/how-to/#video-sync

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