I have a 6thgen Nano, and all the recent songs I've purchased from iTunes wont play at normal volume when connected via audio cable. Can anyone help me figure out why?

This is a semi-new problem, ongoing for several months. I've purchased songs from iTunes before and they play just fine on my Nano when connected to an audio jack cable, but for some reason, anything downloaded in the last few months plays at an insanely low volume. Normally, if I hit the advance button on the Nano to skip to the next song I'll hear a split second of the song at normal volume, but that's it.
I've restored both the iPod and my iTunes (using a Dell laptop, Windows 7) multiple times but to no avail. The songs play fine in iTunes itself, but I've even noticed a decrease in volume when listening to the songs on headphones. I'm beyond frustrated with this as I can't find any support online in the Apple archives, and I can't listen to any of my new music without burning to disc. Any help would be greatly appreciated!!

I have, a couple different pairs, unfortunately, and still no change. TBH, the headphones don't bug me nearly as bad as the fact that I can't plug my iPod into a radio or speaker with an audio cable and hear my latest purchases. Drives me crazy that I can't listen to my tunes!    

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