My iPod Classic skips over audio podcasts from time to time

I really have only noticed this with the IGN Movies podcast Keepin' It Reel. From time to time, generally every six episodes or so (I've been paranoid about it for a while, so I'm not sure how accurate that number it), I cannot play a podcast. I thought it was my old, used, gen 6 iPod classic, so I wound up getting a new gen 7 160GB classic, but the problem persists. I thought I had a temporary fix in that, as long as this was not the last podcast in the group, I would be fine, but I was listening to 2 out of 5 today (third from the bottom), and it just skipped over it and went right back to the podcast I had already listened to.

Furthermore, every time this problem happens, when I connect my iPod to my iTunes, the iPod freezes and I have to do a hard reset. It should be noted, however, that the podcast plays just fine when playing directly from iTunes, and when playing from the iPod while it's connected to iTunes. Is there anyone else that has been having this problem, and how can I fix it?

One other thing, this is a brand new laptop, and I automatically install any new iTunes updates when they come through, so everything should be up-to-date.