iPod and iTunes problems

My iPod and/or iTunes have decided to not play nice in the sandbox, and have taken to crashing. What happens is this: I’ll plug in my iPod to my computer, the Do Not Disconnect message will appear, and then at some point, sometimes immediately, sometimes after I have been fussing around for a bit, iTunes will suddenly freeze. Sometimes it will come out of the freeze by itself, other times it gets frozen and stays frozen. In the latter case, I shut iTunes down, and try to relaunch. Sometimes it comes back up, but most often it won’t. I’ll then try to dismount my iPod via ejecting it in the My Computer window, but then that window freezes too. I then end up rebooting my computer, and removing my iPod when the Do Not Disconnect image goes away about halfway thru the startup boot.

I am running Windows XP, with all relevant updates.
My iPod is a 20GB 4th Gen (click wheel, no color screen).

These are the things I have already tried:
-Checked for and downloaded + installed updates to iTunes
-Reset my iPod
-Gone into the diagnostic mode on my iPod and run the tests (everything passed)

My iPod has just recently started doing this (today, actually. I’ve been messing around with this mess for a few hours now). I haven’t recently downloaded any new iPod software, nor installed any Windows Updates since the last time I plugged my iPod in.

Other possibly relevant info: part of the reason I was trying to hook it up to my computer was that it had started “sticking” for a couple seconds in the middle of songs. I’ve had problems before where it would refuse to play a particular song (play about 1 second of the song, then act like that was the total duration), which had been solved/ gone away after hooking it up to my computer and letting it sit in iTunes for a little.

Any ideas on where my problem might be? Should I be looking for a new iPod?

Um, I just restored it, because a message popped up saying that it was corrupted or not connected correctly. Seeing as I am pretty freaking sure it was connected correctly, and what with the issues mentioned above, I’m just going to go ahead and see what a full restore does. If anyone gives a crap, I’ll update later if it fixed the other issues.

Time for a shiny new ipod! How old is it?

It’s 3 1/2 ish. Yep, it’s old.

Update: I restored it and tried to sync it to copy my music back onto the iPod. No dice. After two songs it would stop. After three attempts at syncing, a happy little message box came up saying that it couldn’t sync (Gee, thanks!). I’m going to try to restore it one more time, and in the mean time will be scouting for a good price on a new iPod. NOTE: No, it’s not cause I’ve got illegal music downloads with viruses. All the files I was trying put back on were either purchased from the iTunes store or off a CD that I own.

Do you have issues with any other USB devices? Try plugging in the iPod when iTunes isn’t open–can you access the device through windows explorer?

I’m not convinced it’s the age of your iPod. I gave my ex my old 30GB 3rd gen, and she wears that little sucker out to this day.

http://docs.info.apple.com/article.html?artnum=93698

I had a similar problem with my iPhone. Tech Support said to completely remove iTunes and quicktime then reinstall with newest version. Cleared up all my problems. The link above is the one they e-mailed me. Sometimes quicktime install files hide on your hard drive, Microsoft has a free removal tool you can download.

ForumBot: Nope, no problems with other USB devices, but, like I said, the iPod shows up in Windows Explorer, but if I even try to look at the icon funny it freezes it.

askeptic: I’ll give it a try, but it’s not looking promising. I’d rather not drop a bunch of money on a new iPod without serious need though, so I’m up for anything.