Trouble syncing iPod Classic after switching from Windows XP to Mac OS X

I'm using an 80 GB iPod Classic (the first iPod classic to come out) and I've had it for a little over two years. Ever since I've had it, I've been syncing it with a Dell Inspiron 1501 with Windows XP Professional. Haven't had any problems since buying it.
I recently bought a 13-inch Macbook Pro, and spent a long time transferring my music from my Windows computer over to this one. When it was done, I formatted my iPod Classic for Mac and tried to sync my library. It works slowly and steadily until the syncing freezes at a random song. Usually after about 700-800 songs is when this happens.
Then my iTunes starts moving very slowly and it's impossible to get the iPod to stop syncing or eject properly. I had to force quit the program and eject the iPod's disc before I could try again. I struggled with syncing in this way about 3 times before I gave up. Now I'm trying to add music manually, a little bit at a time.
However, every time I eject the iPod to see if my songs are getting put on there, it says there is no music. When I go to the "about" screen, it says I have memory on the device, but none of it is music.
I've tried reformatting through iTunes and erasing the disc using disc utility. Anything else I should do?

There are plenty of topics on this very question which gets asked fairly often depending on your search criteria.
Short answer is no.
The OS X license agreement provides for installing and using it on a single Apple branded/labeled computer only.
The only way to install Tiger on a PC is via a hack of some sort and even if the hack is successful, very little on your PC would be supported and the overall performance would not be worth the trouble.
> I was reading an artical and found out that the Mac OS X Tiger already has many of the things that the new windows vista has.
What you read is correct and it took Microsoft 5 years to come up with what amounts to a copy of OS X. I read there are 10 separate/different versions of Vista to choose from? How on earth is the average person (or even the above average person) expected to wade through all that confusing mess?
Apple is getting ready to launch a new OS X version called Leopard this spring which will place Windows even father behind.
If you want to run Tiger and Vista, purchase an Intel Mac which gives you the ability to run both operating systems natively on a single computer.

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I'm not sure if this is a hardware or software issue.
I recently switched from a PC to a Mac. To move my iTunes files (50GB) I simply dragged and dropped them from my external HD to my new computer. I know that Apple does not recommend this process, but when I needed to move my library between drivers earlier this year, it was the only way I could do it without getting an error message that killed the process.
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Hi!
same problem here.I can use around 30G of my iPod Classic 160G.If i try to upload more than that it will take very long time and finally freezes.
Have no idea what to do..

After switching from Windows to Mac, my iPod says "No Music"

I have an 80GB iPod Classic. I used to use a Windows machine, but recently switched to a MacBook Pro. Last night, I copied all of my music over to my Mac, and added some new stuff since I have more hard drive space now. I synced the iPod. All of the files are showing up in the iPod file browser within iTunes. So the media is there. However, when the device is ejected, the only media it says is available is photos. Meanwhile, it does say that I have used 68GB.
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Make sure you authorize the new MacBook iTunes first, and you're good to go, no need to reformat! Hope this helps!
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Hey catwoman001,
Thanks for the question, and great troubleshooting so far! iPod software version 2.0.5 is available for the iPod classic 160GB (Late 2009). If this is your model, you may want to update the iPod. If you are having issues with your iPod, the following troubleshooting assistant may help:
Apple - Support - iPod - iPod classic Troubleshooting Assistant
http://www.apple.com/support/ipod/five_rs/classic/
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Hey bjcondit,
Here is an article that seems to describe your issue and will help you troubleshoot:
'Disk cannot be read from or written to' when syncing iPod or 'Firmware update failure' error when updating or restoring iPod
http://support.apple.com/kb/HT1207
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There are plenty of topics on this very question which gets asked fairly often depending on your search criteria.
Short answer is no.
The OS X license agreement provides for installing and using it on a single Apple branded/labeled computer only.
The only way to install Tiger on a PC is via a hack of some sort and even if the hack is successful, very little on your PC would be supported and the overall performance would not be worth the trouble.
> I was reading an artical and found out that the Mac OS X Tiger already has many of the things that the new windows vista has.
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Don't know if this is the right place to be posting this, but my iPod is currently formatted for Windows. I'm going to college in a month where I will be getting a Macbook. Am I going to have to reformat my iPod and will I then loose all my music/photos/etc...?

Use the instructions in this article to transfer the content; if you can locate the photos on your hard disk, they can be moved over in the same way. Reformatting the iPod is not necessary, but may be useful after you've transferred all of the content over.
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THANX

Pros:
1. More pleasant internet experience - pop up filtering much less painful.
2. Virus attacks practically unknown of.
3. Operating system (OS) interface is much more intuitive and I believe easier to navigate through.
4. OS crashes/hangs less than once every 3 months in my experience. If it hangs up it usually is a program that needs updating and quitting the program leaving the rest of the system running. Extremely rare to have the system freeze up. Never saw a blue screen of death.
5. Security is a big plus.
6. internet Apple shopping and support is highly rated. My experience with service turnaround is much better than any PC company (I am thinking of my Sony experience that took 6 weeks for a simple CD burner power switch repair and Dell onsite repair with the tech breaking the laptop case and needing to send it in anyway with a 10 day turnaround). I needed a screen replacement from Apple that took 3 days door to door with overnight shipping under warranty.
7. Multimedia experience has been great - iMovie, iPhoto, iTunes, iDVD
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1. Some web sites are Explorer friendly only. Explorer has not been updated for OS X in years (which is probabley a pro since it is a mediocre browser). Firefox, Netscape, Safari, may not completely display everything properly.
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3) Some of these files on the PC are very large (1-5GB), is that a problem to move them using the ipod?
Thanks for the help!
JV
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1. Yes.
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If I buy a Mac, can I move my iTunes files from my PC to my Mac? My iPod is configured for Windows. Can it be reconfigured for OS X or do I need to buy another iPod?

Assuming the library is in the usual location on the PC and consolidated, i.e. all files are in the *C:\Users\<User>\Music\iTunes\iTunes Media* folder:
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Trouble syncing iPod Classic after switching from Windows XP to Mac OS X

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