NEW TO iPod...Need assistance on pitfalls to avoid before I buy!

I am contemplating purchasing the 160GB iPod Classic and am an active Windows XP user on a regular PC. However, I have seen multiple posts/news articles about the new iPod Classic not syncing with the new iTunes version 9...
I would hate to purchase such a great product only to find out that I am unable to upload my current music files to the iPod (basic WMA or MP3 files), or encounter other unforseen issues.
Can anyone please provide any insight into what I should be aware of before making this purchase? THANKS!!

i think issues with itunes should be the least of your worries, as those can always be fixed with firmware updates. i would be more worried about hard drive failure with the classic
just keep in mind that any hard drive based ipod like the classic has a good chance of crashing or failing on you if you don't take proper care of it. Unlike flash based ipods like the nano or the ipod touch, you have to be wary about taking the classic out on jogs or any activity that involves a lot of movement and shock for you ipod. Also if you drop the ipod enough times or expose it to extreme heat/cold, you are probably going to get some type of hardware failure with the classic. i would consider getting the 64gb ipod touch instead although it does cost more money, but I feel it's more reliable and I think in the long run, the Touch will have a longer lifespan than the classic and will still be relevant in the near future. I've heard reports of Ipod classics lasting only about a year or even less before experiencing some type of problems. But perhaps that's only a small percentage of people. However, judging from past experiences, I used to have a 20gb hard-drive based ipod that performed well for about 10 months before dying out, and I very rarely ever mishandled it.
But if you must get the classic, then invest some money in a good case or protector and be sensible about how you handle and use it. Otherwise, I do think it is a great product for people with large libraries.

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