I wish upgrades were easier on the iOS side, but in some instances users are demanding new features. Take for example split screen on the iPad. I takes time to figure out what your interface should look like in different dimensions. I am not sure what Apple could have done about that in advance.

Upgrades on the web take time and resources too. So I don't think this is unique to iOS.

I guess it is a general software problem. Breaking changes in the platform forces developer to put effort into keeping application functioning and that needs to be paid for somehow