Ipod freezing itunes, the last problem in a long list

So ill start from the beginning with the problems ive had with my ipod...
The first problem i had started maybe 6 months ago. My ipod would just stop playing when it played certain songs. Everything else worked fine, it would just stop sometimes. Then in the last few months it stopped being able to connected to a computer. Whenever i would hook it up it would just automatically eject itself. I tried hooking it up to a freinds computer and for some reason when it was hooked up to his computer it worked fine. I decided to just do a restore at the point hoping to end all my problems. The restore went fine. I started putting music back on it and i started getting error messages. The computer said that my ipod was missing the file that would allow me to sync with the computer or something like that. I tried to restore it again and it didnt change anything. In the last couple days i tried to put music on the ipod again and now it wont show at all in itunes. The ipod says its connected but when plugged in itunes just freezes.
I dont know if it makes any difference but my computer is a mac, and the computer i was able to do the restore on runs vista.
Im totally out of ideas and im not sure what my options are from here. Any and all help would be awesome.
Thanks in advance everybody!

I get exactly what your describing and I noticed we are using the same laptop!!
I did not notice originally as I've got an old 40gb click wheel, about 3/4 years old. The battery is not great so assumed it may have been that but even fully charged I'm getting no luck.
I also followed the 5 r's and all the other suggestions for Ipod in My compute but not in itunes but nothing has worked. I cannot get my laptop to recognised my ipod via Itunes but it see's it fine via My Computer.
Both the Ipod and Itunes work fine without each other, Ipod plays songs fine etc and Itunes downloads music from cd etc and still performs all the usual functions but nothing else works.
I'm desperate for help as I run every day and buy a new cd each week and at this rate I'm going to have to dig out my old CD player!
Also just a point of note I looked the price to get my Ipod serviced as I figured this may help but the price quoted from apple was £160+...you can get a new 30gb for less...talk about customer explotation!!

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