"I'm not the administrator on my own hardware (without jailbreaking)"
I'm an android user and definitely think Android is the better and more open choice, but this point is just as true on Android as it is on an iPhone. Getting root may be easier than jailbreaking; I've never jailbroken an iPhone, but the point is that even on Android hardware which you purchase directly (not subsidized by carriers), you're not the administrator on your own hardware.
I looked into getting root on the G1 - it appeared to be hugely more complicated than the pretty simple jailbreaking process, involving downgrading the OS to find a local root exploit. I didn't bother, it looked like far too much bother for too little reward.
Interestingly, the Nexus One from Google allows users access to the engineering bootloader (allowing re-flashing with a rooted image) with a simple command sent over USB ("fastboot oem unlock"). There's even a friendly "third-party images are not officially supported" confirmation screen built in.
I think that's actually why there's not a click-and-it-does-it solution for the G1 - because there's far less restrictions on what apps you can install on the device there's much less incentive for people to 'risk' fiddling with it.
Tethering is probably the 'killer app' for jailbreaking/rooting on both platforms for most people, but there's a lot more to be gained by jailbreaking your iPhone.
Having said that - I haven't bothered to re-jailbreak mine after the last few updates since I realised I never used the jailbroken features.
So Android won't be any better, I was hoping for a less supervised computing experience. Something as simple as copying files to and from the device, or installing/compiling software on it is not the default approved behavior.
Well it's not that bad on android. You don't have root but everything you mentioned is "allowed."
Although not having access to root annoys me in principle, I haven't needed root for anything, so I haven't bothere rooting the phone even though it's fairly trivial.
I'm an android user and definitely think Android is the better and more open choice, but this point is just as true on Android as it is on an iPhone. Getting root may be easier than jailbreaking; I've never jailbroken an iPhone, but the point is that even on Android hardware which you purchase directly (not subsidized by carriers), you're not the administrator on your own hardware.