I've got the same problem (80GB iPod classic). For me, it's much more than 3 or 4 albums; I'm probably somewhere in the known range of 30 or 40 albums affected--I don't know how many untested albums are also affected. I've got the same weird connection behavior, too, only on Windows. (The ipod routinely fails to appear unless I reset it first, or will sometimes fail to disconnect when I try to eject it. The iPod appears to be stuck in a loop of ejecting and then re-connecting.) I'm not sure whether the connection problems are related to the skipping mp3s or not; they might just be indicative of something else wrong with the iPod.
As far as a solution goes, there is one suggestion that seems to work: delete your ID3 tags and re-create them (from within iTunes, using track info from the iTunes database). You'll lose your album art and potentially other custom ID3 fields, but it seems to cleanse the tracks out well enough to play on the iPod classic.
This isn't a real solution, though, as it requires manually fixing an unknown list of files. (Since the tracks work fine in iTunes, you have to discover them while watching the display of the ipod - the tracks skip by so fast you likely wouldn't notice during regular use.) Also, since it's a destructive fix, I certainly don't want to apply it blindly to my entire library (and any future files coming in).
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I've thus far been unable to find anything consistently "bad" in the ID3 tags of these skipping tracks, but then I'm no expert on the intricacies of how ID3 tags are created or attached to the files. However, by virtue of the fact that the files play just splendidly in my old iPod photo, as well as iTunes, Winamp, Foobar, Windows Media Player, and anything else I've tried them in, I have to conclude there's something amiss with the iPod classic firmware. I'll add here that the first time this happened, I exchanged my iPod at the place of purchase, but the new one does the exact same thing. (I don't have any other iPod models to test these files against, however.)
The mp3s I've been looking at were all ripped from CD myself, on Windows, using EAC and LAME (a common configuration). Now that I quickly compare the track info between an original (non-working) track and a fixed (by my method above) track (via the file properties window in Windows Explorer), it appears as though the tags on the "good" track are truncated. For instance, the Album title on my "bad" track is fully:
Balanescu Quartet - Byrne, Moran, Lurie & Torke
whereas the "good" track is shortened:
Balanescu Quartet - Byrne, Mor
Perhaps there are conflicting sets of ID3v1 and ID3v2 tags, and the iPod classic is getting confused. I'll add that a good portion of my affected library is Classical (suggesting long track or album names) or World Music (suggesting an alternate character set). I think this will be my next line of investigation.
In the meantime, what's the best way to actually get an Apple engineer to chime in on this issue?
