Firstly, around the time this started (~2009), Apple was starting to make OS upgrades free for a bunch of users for instance. Their software rarely failed to install, and almost never threw weird errors around licensing. Neither did Android's.

And secondly, remember what I said around being the underdog. Apple had first mover advantage in this field, they could afford to make their tools a little more annoying and still have developers sign up. Microsoft was the underdog, they should have given away a free copy of Windows with all the Visual Studio crap preloaded to developers; that would have gone a long way towards getting developer mindshare. But that would not have made sense to the revenue obsessed execs at Microsoft, and so did not happen.