I was in their walled garden for a while. Three iPods and three iPhones over time, just for me. But the constant issue with dead devices and getting media from one item to the other (initially) was a pain, but as they opened things up a bit, there was still problems sometimes with accessing apps and media, as well as the overall poor experience of iTunes on Windows. I just finally got tired of all the bullshit, bought an Android phone and sailed off into the sunset, so to speak. Anyone who's left Apple's phone environment in the past remembers the issues with iMessage and not getting texts on your non-Apple phone from anyone in your contact list for quite some time.
If you're in their garden, it's not horrible. Especially so if you have a family and all use it. But as soon as you leave, you understand the issues with all those things that could have been standards and easily portable, but were not: media types, charger types, methods of accessing phone data, methods of porting media from walled-in devices to things outside of it, etc.
One of Apple's biggest successes isn't just their products or content delivery. It's the sandtrap of getting you there and using things, only to realize it's more convenient to stay there. "You can check out any time you like, but you can never leave."