Comment Interface Builder (Score 5, Interesting) 216
The biggest problem I've had so far is Interface Builder. It isn't the most intuitive piece of software. Dragging and dropping to connect button actions to methods between two pieces of software (XCode and Interface Builder) that don't actively sync with one another, at least not as I've yet to find.
I already had the C/C++ and GUI/fat client app building experience from 10 years back.
+fragbait