IPod shuts down, comes back, shuts down, etc...

Question

I have looked on the board for this problem, and have found a few similarities, but none that actually match my case. So, here goes...
First of all, my iPod: he is a very old 20GB iPod, a gift from Christmas 2003, and I have been considering replacing him or his battery, but I'm not sure that replacing the battery will fix this problem and I'd really rather not shell out $400 when all I want is my same iPod only working (I've got no interest in getting a new color iPod that holds a bazillion songs and plays videos and mixes songs and predicts my future and can save the world and everything--I just want to listen to music, that's all).
Anyway, so the problem is as follows: my iPod worked fine for about two years, aside from some minor problems (for example, sometimes if I clicked on a song he would think for a few seconds and then move to the song after it--but all I'd have to do is go right back to the song I wanted to play, and there would be no problem). No real difficulties charging, holding a charge, going to sleep, waking up, etc.
Then, last summer, I joined the cross-country team, and wore him when I ran, and he started having more problems. I have a little blue iPod belt-pack that I wear when I run, and it's supposed to keep the iPod from bouncing out and crashing onto the floor, which it does. However, it does not keep him from bouncing, and I think this is what started everything. I have a certain playlist that I listen to when I run, and sometimes he'll finish one song and the bouncing will mess him up and he'll skip several songs and move to one towards the end of the list (and refuse to play the skipped ones, even if I click on them manually--he'll just skip right over them again). I'm fairly sure it's the bouncing because I have noticed that if I run more slowly and softly when he's finishing a song, it reduces the chance of him having a hissy-fit and skipping the next seven songs.
(I should probably note here that he does not always skip the same songs, and all of my music plays fine most of the time, so it's not a song problem.)
Anyway, shortly thereafter he started having battery problems when I ran--occasionally he'd crash in the middle of a run, and display his Angry!Battery! sign when I tried to turn him back on. Annoying, but he didn't seem to have problems any other time, so I'd let it slide.
A few weeks ago, however, he started having SERIOUS battery problems. I'd be listening to him when I was doing homework or reading or some other mundane activity that involves little to no real motion, and he'd suddenly shut down after about half an hour and display his Angry!Battery! sign at me when I tried to turn him back on.
So this went on, and I got very frustrated, blah blah blah, and then he started being a NEW kind of broken.
Now, he'll shut down with no warning (although I have noticed that it happens quite often when I am scrolling through a song--it's not nearly as frequent when I just listen to a song all the way through), but turn back on when I try to turn him on. The battery is displayed as empty, but it refills itself as he plays, until he suddenly gets mad and shuts down again. Sometimes, I can turn him back on, and he plays for a good amount of time; sometimes, I can turn him back on and he plays for about a minute and then dies; other times, there'll be an Angry!Battery! sign and I have to plug him in.
So, to recap my most current problem, because this post is getting long:
-iPod shuts down randomly
-iPod turns back on, shows empty battery, but plays anyway and battery slowly refills
-iPod shuts down again after about half an hour
-iPod occasionally turns on and plays as normal, often for as long as an hour; if not, iPod either turns on and shuts down after a few seconds, or shows Angry!Battery! sign and refuses to turn on.
Also I should probably mention that my brother got an identical iPod for Christmas the same year, and has never run with his or really used it for anything except listening to music when he studies or drives (he has one of those car gadget things), and doesn't have the same problems.
I'm thinking it's a battery problem, but the fact that sometimes he'll shut down and then come back and play for his usual amount of time (remember, this is a 2003 iPod, so the battery has never been as powerful as the new ones), and also the fact that it happens most often when I am moving through a song, makes me wonder. Should I pay the $60 to replace the battery, or is it time to just get a new iPod? (I really miss running with music.)
Thanks!
-Brooke
Dell Dimension 8300   Windows XP

Answer 1

It's not the tracks that are causing it to freeze up. It's random!
All these tracks have been on my iPod since day one and played fine and most of them are from iTMS anyway.
So your suggestions is not quite relevant.