My first smartphone was an iPhone. Most things were counter intuative. I also had to jailbreak it to do the things I wanted. A lot of it was basic stuff. The one I remember was that I wanted to use certain Bluetooth devices that would only work when jailbroken.

Once I tried Android there was no turning back. I've used Apple devices for work and it is still counter intuative but things like Bluetooth are less restrictive at least. Still you shouldn't have to try to break or hack the system you're on to get basic settings that aren't available by default.