I dread helping anyone with iTunes related issues. The syncing process is dangerous, it's far too easy to wipe someone's collection of music / family photos / pictures. I'm not sure if this is an isolated issue but I start sweating bullets as soon as I have to connect an iDevice to iTunes. What really shocks me is that instead of showing a big red warning message before a destructive sync, it silently goes ahead and wipes data without even asking. And there's no easy way to tell what a sync is going to do. After any iTunes sync I generally think "Ok, now let's assess the damage".
To add insult to injury it's almost impossible to make a file-for-file backup before decimating a device with iTunes sync. In fact, the iTunes sync process is the main reason I stick to Android despite it having a whole other ecosystem of flaws. I'll take a USB Mass storage device and robocopy / rsync, thanks. They actually work.