iTunes is the single biggest reason I will never own an iDevice. While it is somewhat accetpable on a Mac.... like all Apple software, it blows goats on a PC.
As for iOS vs Android, you have to draw a distinction between the operating systems themselves, or the iPhone vs <insert android phone>.
Apple has been playing catch-up lately in terms of features, but they are doing a decent job of including features and usability that most people will find acceptable. The downside to the iPhone is that you only get one form factor and one way of doing most things. Jailbreaking (if available) helps, but at the end of the day it is still Apple and your service carrier calling the shots.
Android requires a more informed user/customer, and you may well have to educate yourself about how computer/tech works in order to figure out how to do something (or do it more easily). Android is having growing pains between being a straight-up operating system vs an entire cloud/computing/media/communication platform (and all degrees in between).
I consider it the platform of choice if you don't want to get nickel&dimed for every last bit of media or programs that you consume on your device. There's a reason that Apple is one of the most profitable companies in the world. All that $$ comes from their users.
Short story is:Choose whichever is the least infuriating to work with day in and day out.