Let me start by saying I'm technology agnostic, and have no special place in my heart for Microsoft or Google, but I'm just plain tired of trying to avoid Apple's stranglehold. My primary beef with Apple is their philosophy of "pretty but restricted" delivery of technology. I will give the user a simple software and player to deliver music, but I will control it with digital rights management limitations, and I will force you onto my platform.
I bought my first .mp3 player in 2003 to run with my music. iPod's were nowhere at the time, and to load files onto my player I simply dragged .mp3's onto the player drive and viola! Oh, and it had an FM radio. Then Apple comes onto the market and I can hardly find good players like the original SanDisk Sansa's out there any longer. Transferring, synching and organizing my music in the iPod universe stipulates that I use iTunes. Thanks, I don't need a software application to load music onto a (portable) hard drive. A friend just spend two days trying to figure out how to back up and migrate a music library HE PURCHASED legitimately to a new home media server.
The biggest challenge getting off Apple creates to me personally is the ecosystem they have created around their devices. If all my friends use iPhones, it's must harder for me to live in an iPhone world and simply make my own mobile device choice and co-exist with everyone around me. I loathe restrictions. Simply. Period. I don't want to be locked down to any service plan, application controls, synching/ loading software, etc. I have owned an iPhone and a 3G iPhone, but find my current Blackberry Bold better in many ways. And none of these gave me the mobile computing features that plain old Windows 5 on my Blackjack or Blackjack II gave me. And none of these gave me the simply pleasurable user experience that I had with my old Motorola Razr.
I guess my basic point is this: I'm elated to see the suite of new mobile devices emerge on the market lately: Droid and Pre and Pixie and HTC touch phones and others. I think I am starting to feel the "walled garden" approach to Apple's stranglehold lessen. The basic philosophy of, "I will limit you but make your user experience very nice" has always seemed very, "master planned community" and very, "dumb it down for the masses with cute icons" and, "mediocre is good enough for you because I'll make it simple." It's like eating at Applebee's... it's never going to completely fail, but it's also guaranteed to never be a 10 out of 10. And I personally find mediocre very boring.
Technology follows trend, and we saw a similar approach to Internet access with AOL in the early days of dial up. "let me control your experience but make things simple for you" eventually gave way to, "hey, I don't need you to get on the Internet and I rather an unrestricted experience, thank you very much." I'm watching from the sidelines and silently praying for a flight to quality, and this either driving draconian technology philosophies away, or giving birth to a new era of diminished controls. I'll be watching, eating my popcorn, cheering the release of each new Android phone release, hoping for a comeback of Windows Mobile, and periodically dusting off my pile of discarded iPods I refuse to sell on eBay because it's my duty to keep them out of circulation in the spirit of liberating the music and general freedom from oppression.