Help Mac user help new Vista user - install itunes or not?

Hi,
My friend has a new Vista PC and he's not a skilled user. I'm a Mac person myself. He's having tons of trouble with it and I live 2000 miles away. I'm here on a visit and have been helping him get Flash player and Yahoo IM etc installed.
Is iTunes a simple, painless, installation or does it require troubleshooting? If the latter, then we won't even try. Too little time for anything but install-and-play.
Your advice will be much appreciated.

Our luck will be problems out the wazoo. His PC is brand new and shiny, but working with it is like trying to do eye surgery on yourself without instruments or anesthesia: painful.
Maybe we'll postpone this until I buy him a Macbook later this year.

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