What you are labeling as brand image is also dedication to usability that no mobile competitor at the time had. It's not that iPhones "seem hip" so much as they don't make you feel like a fumbling idiot when attempting complex tasks
The technology learning curve is less steep with an Apple product, but the capabilities of the device eventually hit a wall, unless you are willing to undertake the additional effort of learning to jailbreak. Competing devices have a steeper learning curve, but they go all the way up to the hardware ceiling without such a big discontinuity. Rooting or re-flashing an Android device is still a leap, but it is much less of a shock to someone who has gone to that point. In comparing Apple and Android devices, I'd say that stock Android is more capable, but Apple is more user-friendly. Carrier-crippled Android devices reduce the functionality to that of an Apple device or less, without the mitigating factor of the superior user experience.
It turns out that doing all your user hand-holding with soft, warm hands has significant market value.
That seems like a relatively simple and common thing to do for an Internet-connected device. Is the hardware capable of doing that? Is the software capable of doing that? Does Apple corporate policy allow customers to do that on the devices they own?
Ok, granted, the average mobile user does not block ads. But how about moving photos off the device, or loading existing music files onto it. Can I plug in a standard USB cable and mount even a portion of the local storage of the phone as removable storage on the desktop computer?
The problem with this line of thinking is it ignores the needs of the vast vast majority of current consumers. Most don't ever hit that wall you insist is inevitable. The ability to hit the hardware ceiling, via the investment of a steep learning curve is not attractive or necessary for most people. You are not a model consumer.