iTunes under Wine isn't exactly something that you could easily do, but is possible, though the tests show that iPhone detection doesn't work. I remember seeing a USB patch for Wine a while back, but you're better off using a virtual machine or dual booting.
I'd dual boot, using Windows strictly for programs and apps that do not run under Wine. However, if you do find this to be a hassle, I'm not stopping you from using Windows, though I will point out their unethical actions, especially in Windows 10.
If you do decide to go with Linux (dual boot or not), I'd recommend using Xubuntu, as you rarely have to use the command line, as well as having a light-weight desktop environment without the Unity spyware.