Though I'm reluctant to play the Zune card, I've been impressed at the support Microsoft has continued to give even the first generation devices released in 2006. That my wife's Zune will continue to get software updates wile my original iPhone is now frozen in time is a little sad - as is the fact that her Zune does wifi sync and FM radio.
OSX Snow Leopard only supports Intel processors (2006), Leopard only supports G4s @ > 867mhz (unless you hack around). I've installed Win7 on computers from 2001 with no hassle, and with improved performance over Windows XP (let alone Vista)
I really do like my iPhone, but it definitely feels like the software shortcomings have been forced by Apple - sort of like how my phone's hardware is perfectly capable of MMS, but official software won't allow it. My phone records video quite nicely with Cycorder, but I'd have to purchase a third party app that functions at a fraction of Cycorder's quality if I stuck with official updates. And now I don't even get to try the new OS unless I upgrade.
It's still a very capable device though, and I'm more than capable of deciding not to upgrade my phone hardware until my current phone hardware ceases to function as designed.