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Reinstallation & Freeze: Which to Fix First?

Both of my problems have appeared separately on this forum but alas, no one apparently has a had a tag team of issues so I pose this question: which to solve first because I fear I may lose all of my music...

1. I had to reinstall my OS (now running Mac OS 10.3.2). When I did that, I lost all my music. I was aware that I could put it back w/ 3rd party software and even went so far as downloading and paying for PodWorks. I got scared to do it because when plugging the Ipod into the computer it automatically updates and I couldn't seem to get it to turn into "manual" mode. So, I have this friend who said he would do it for me. So I thought I would wait, and then murphy's law...

2. I get the "freezing" problem that is mentioned frequently on this forum where my ipod plays silently and none of the buttons work, even the lock. So my problem is difficult b/c I can't do a hard install or whatever it's called b/c the minute this thing connects to the computer, I'm afraid it will wipe out all of my music.

The question here is then what is the systematic approach to fixing this. BTW Ipod is playing on and on b/c I can't seem to turn it off and when it goes into the charger (not connected to the computer), the charge icon does not seem to be working.
[1316 byte] By [kvogs] at [2007-11-9 20:23:39]
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