Well, iTunes is a pre-existing ecosystem left over from iPod world domination, so a large number of potential customers already have their music (often including purchased mp3s) on iTunes and in Apple's proprietary format, plus are in the habit of sinking their device to it. Otherwise, starting from scratch I don't think the music experience is actually significantly worse.
As for smartphone usability, an iPhone arrives with all usable apps in icon form already on the front page wher you don't have to look for them, and when you finally stumble into the app store the installation automatically installs an app icon at the nearest opening on your pages. When you get a Droid, there is software and widgets you don't have to keep on your home page (but you have to know how to remove them), and while the app store installs to your phone just as easily, you have to navigate a window to get a quick-launch icon to put them there.
I purposely picked the most basic part of the experience...because if people are using their first smartphone these are the sort of things they will experience in the first 2-30 minutes of use. Now, I know that Android has a little robot that explains a lot of this stuff to you, and it was obvious enough to me that I turned the little robot off before I left the store (DX is my first Android device), but if you aren't a teching the Apple hand-holding model definitely provides a soft landing when you first starting playing with it. There's just less to learn.
Likewise, whether Apple's installed apps have the features or not that you want, you never have to worry about seeing if there are better apps in the market, because Apple doesn't allow that sort of competition. But if you want a good email client on Android (aside from Gmail) you have to look at the Android market, perhaps find some sites on line to read reviews of (or else spend time reading the not-always-helpful marketplace reviews) and try to figure out which one will suit your needs. Or else try them both. All of these are ideas that take more confidence in your own skills and knowledge of the device.
When people say "it just made sense" what they mean is "I had no other options so I could quickly learn what it did". And while as a power user it's easy to look down on that sort of response, a lot of consumers want that in a device they rely on.
I personally almost always recommend Android over iPhones, but that's because the people who ask me are also reasonably savvy with technology. If my parents decided they really wanted a smartphone, I'm not at all sure I'd recommend Android to them.