Skips 2 nxt song halfway through playing

Question

What is wrong if halfway through a song my ipod skips on to the next song even though the previous one isn't over? It happens all the time and can't listen to half of my songs.

Answer 1

Well Drake Bradley, it wasn't THAT drastic of a solution. I just unchecked the only playlist that I had synced to the iPod and then told it to sync, thereby removing all mp3 files from the iPod, and the re-checked and re-synced. Unfortunately, while this wasn't drastic, it also wasn't a solution. The same files still fail to play properly.
However, I've determined pretty conclusively that the iPod isn't the problem. Silly me, I went to all of that trouble of re-ripping tons of songs right before my vacation, and I never bothered to listen to any of those songs in iTunes until today. Same problem in iTunes, completely independent of the iPod. The only difference is that iTunes doesn't get hung up for several seconds without knowing what to do - it hits what it thinks is the end of the file, and immediately skips to the next track, upping the play count as if it had played the file all the way through. I've watched the little marker that shows how far into the song you are as it scrolls across... as soon as the time elapsed and the time remaining match, it jumps immediately to -0:00 (the end of the track) and then plays the next one. It's as if I had edited the file's Options and set "Stop Time" to halfway through the track. (Exactly halfway makes sense - the old file was 96 kbps, the new file is 192 kbps, and 96 is half of 192.)
A few interesting things that I discovered after further experimentation:
1. I can fast-forward past the halfway point of any of these files, and it will play the rest of the song just fine. It's only when it actually hits that "halfway" point that it skips. So the full song is there in iTunes and on the iPod, it's just thinking the end of file is in the middle of the file.
2. Just to see if the problem was intrinsic to the mp3, I tried to play a few in RealPlayer (the application that I used to rip the songs). They play fine in that application.
3. Removing the songs from my iTunes library and then manually re-adding them to the library appears to fix the playback problem. However, all data that was specifically set in iTunes (album artwork, play count, date last played) and not intrinsic to the ID tags is lost when I do this. I would find it irksome if I had to lose all of that data for hundreds of songs just to get them to play, but I suppose I could live with it.
Your suggestion about re-encoding in AAC format just isn't gonna cut it, because I have several hundred files that I'd have to do this for. I've experimented with the iTunes encoder - it does its job just fine, but I don't like how it names the files or what folder it puts them in. I have to manually delete the old duplicate files from the library. That's a pain. iTunes should be able to recognize that a file has been modified and bring in all data relevant to the new file, even if it has the same filename as the old file. One thing I did make sure to do when I re-ripped all of those songs was to click "Edit Info" in iTunes after highlighting an album's worth of them, and watch as the bitrate updated to 192 and the album artwork disappeared (which I then re-downloaded), and iTunes seems to understand that the file changed, but is still ending at the point in memory where the old file ended. It's a bug in iTunes. I will report it in great detail when I talk to an Apple technician on the phone later today, and I will expect that they will fix it by the release of iTunes 9 at the very latest.