IPod freezes when playing from a docking station...Any ideas about a fix?

I have had my current iPod for a couple of years now, and until recently it has worked flawlessly. Over the past couple of months a problem has develoed when I play my iPod from a docking station. When I play the iPod from it's cradle (connected to my HK Soundsticks) or from my JBL Speaker Base, the iPod plays fine for the first few songs. After a few songs, the iPod stops in the middle of song and skips to the next song, then skips three of four times without playing at all and utltimately locks up completely. The problem seems to arise when I am simultaneously playing and charging.
Any ideas?
I am using a 40mb, clickwheel, iPod.

All I can suggest is to re-encode the video as m4v with QT Pro, there might've been a problem in encoding. Also, try sending this same video (setting TV Out to Yes) with the iPod not plugged into the dock and with an Apple RCA cable, if you have one, hooked up to a TV. If that works, the dock connector might be damaged (unlikely) but it's possible. So once you've re-encoded, see if the dock situation works then. Good luck.

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