Song pause/skip at the beginning of each song

I've recently been experiencing my music pausing for a second when a new song starts playing. The music will just stop playing for a short time after the song has begun. Sometimes when I quit iTunes and open it back up, the issue is resolved temporarily... But eventually the songs start skipping again. I have the latest version of iTunes, but I'm not sure if that's the reason why this is happening.
Any suggestions?

This sounds just like what happens on my Rio Karma and my 5G iPod when I play certain albums containing tracks over 10 or 15 minutes long. Gapless playback isn't quite perfect in these cases, because I think the devices simply don't have enough memory capacity to buffer ahead when they're dealing with such long files.
I really don't know how to solve your particular problem, and I don't think I've ever experienced this in any version of iTunes since 7.0. It sounds vaguely like a memory/buffer handling problem to me, though. Do the playback problems coincide with anything obvious, such as a large amount of Internet activity with media file caching and so on? If so, I might start by checking your browser, QuickTime, and other application preferences to keep them from caching or at least set some minimal limits. I have been using Cache Out X for years and setting it to run at login and clear Internet-related caches, and I believe this has helped at least to some extent in improving overall application responsiveness and performance.

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