Yes, I completely see that. This is not a black or white question. You can use Windows, MacOS, Linux, Android, iOS... and learn close to nothing or you can geek around hour after hour to expand the boundaries of your device.

I would just assume, that you learn less if everything you want to do, works out of the box. And 'working out of the box' a typical selling point of the Apple ecosystem. Which of course doesn't mean that you can't have a steep learning curve. Your use cases obviously weren't delivered out of the box, so you had to get creative as well.

I had a jailbroken iPod Touch with a shell on it and spend hours and days overcoming system boundaries just out of spite. I also remember vividly trying to bring mobile games to a Symbian phone, tweaking around with a HP iPAQ on Windows Mobile, manually typing Midi ringtones with a text editor on a Nokia. :D