I need help transferring a PC using iPhone 4 owner to a Macbook Pro purchased today. My curiosity stems from a situation that happened in December. At that time a friend had an iPhone 3GS that had never been sync to any computer for over a year. The phone was a replacement for a broken iphone. Apparently the people at the Apple Store never told her that she needed to sync the iPhone with iTunes every so often. When she finally sync'ed it in December, iTunes did not recognize the iPhone (since it was never sync'ed) and wanted to start it as a new phone. The iTunes sync kept all her apps, emails, and contacts but deleted her music and over 1 years worth of photos, including the behind the scenes photos of her own wedding. She was very pissed and it's a flaw in the iTunes/iPhone environment that Apple needs to clarify. That catastrophe would never have happened on Android or RIM phones. So back to the question, how do I make sure that my other friend that bought a Mac today doesn't make this mistake and start hating Apple from day 1. Does she need to transfer her whole iTunes library from PC to Mac? Will this transfer all of her iPhone backups? should she import her iPhone photos into iPhoto before syncing with iTunes on the Mac? Any advice?