hey
there is no iTunes build on the raspberry pi however there are some things that will work like iTunes that are available but you shouldn't need them because you can just use your iCloud to back every thing up it may mean that you have to upgrade your iTunes but it is not to much $
and about your 2nd question when you first enter the pi you can hit shift for recovery mode but when it boots just open it .
not sure if i was any help but hope i was