Songs skip (or completely stop) and other strange glitches

Question

For a little more than a week now, my 2nd generation iPod Touch has had a number of problems.
-Firstly, some songs skip, though it's not your typical skipping like you would hear off a scratched CD. A portion of a song that's probably less than half-a-second will repeat about once or twice and the song would then continue. It is actually much more annoying than it probably sounds. I would not say that the file types of the songs are the problem because I have been able to play one of the skipped songs in its entirety twice without any problems. All the files that have skipped are MP3 and some of them had been converted from WMA.
-Sometimes when a song has skipped, it would just plain stop later on. Sometimes it would return to the main menu or sometimes all the way back to the home screen. I then would go back to the music section and the machine acts as if the song was not playing to begin with. One time I clicked the music button and it brought me to a Playlist that I had not been playing at the very moment the machine stopped. What's up with that
-The time tracking on a song can get completely wonky. You try to skip to one part of the song and it can sometimes sound way late compared to what's going on the little display at the top of the screen or it could have suddenly stopped and the display would say it's still playing. This is a pretty minor problem, however.
-The weirdest occurrence to have happened to the iPod was when a song stopped and the machine returned to the Home screen...but with the song display at the top screen. You could click buttons like Pause and Play but it's all on the home screen and nothing is computing sound wise (no song is playing, by the way). This is probably impossible to imagine in your head and my description is foggy at best but this is the most worrisome of all the flaws with the player and though it only happened once it sounds almost too bizarre to be preventable or repairable.
What I have been doing recently with with iTunes - if this information is any help - is 1) creating tons of Playlists and 2) adding album art from my computer. I would basically save images onto my PC from the internet, regardless of what kind of files they were. I would then copy the images I had saved onto my drive to iTunes. Would this be a possible problem, if the iPod could not read a certain type of image? Or is it that all the work I've been putting my iPod through the past couple of weeks, immediately filling the thing with 1700+ songs the first day and then doing all this playlist business?
I honestly have no clue. You can say that I'm perhaps asking for too much but when your player hiccups and the song "Now Playing" completely dies it can ruin your enjoyment. If there is anyone who can help me, you have my fullest gratitude.
Thank you in advance!

Answer 1

Funny I found this post on the exact date that you posted it. I am having the exact same problem that you are (with regards to the song restarting the first couple to a few seconds into it - even one song not being playable partway through it). I don't think my identical problem is quite as severe as yours, though. I was doing the same thing as you: editing album art to songs with images essentially from the Internet (the images were of large dimension) to high bitrate-songs from large albums in rapid succession. I would go to the "get info" window, click the "artwork" tab, click in the album art field and copy paste, paste, paste one right after the other... I think this is causing our issue as the songs played just fine before. I've done a bit of research into this and one apple tips forum told me to right click the song and click "convert ID3 tags" and some other non-helpful stuff that I won't disclose yet for fear that you might get yourself deeper in the hole. But I'll tell you if you'd like. All in all, I am having the same issue and I need to resolve it because iTunes screwed up my mp3s that were just fine before sans album artwork. I even have those albums backed up on my external hard drive - with the ID3 tags edited and the songs corrupted! I wish I knew how to remove the headers. Anyone know how to fix this?