Chosen Solution
I was looking through a bunch of old stuff and found an iPod. I plugged it in and it took 2 hours to actually turn on. It dies in about an hour or 2 and the iPod makes a very soft click when it turns on or tries to play a song after sitting for awhile. EDIT: I tried went to replace the hard drive and the battery was poofy (for loss of a better word). Could that be part of the problem too? EDIT EDIT: I finally ordered another battery because the whole thing crapped out. I should be able to carry all 4627 songs with me again on Tuesday
The hard drive is bad, replace it
