You wrote "upgrading to Vista." That's not a clean path to Vista so most owners are caught unaware about the need for drivers, new firewall, antivirus and more. So my answer is yes.
All I've heard is when you plug an Ipod or an Iphone into a windows vista pc all you get is problems. Like my friends Ipod worked perfectly for a year and a half till he got his new laptop with windows vista and now hes constantly restoring and doing updates and restarting it, and my other friend got a new Ipod and all its done is screw up also used on windows vista and I also heard you can't sync photos on vista to an Ipod or Iphone and I just wanna know if anyone else is having these problems? Because I'm a proud Ipod owner and wanna know if upgrading to Vista will cause my Ipod to become a nice paper weight.