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Yet for some reason it doesn’t seem to matter that iOS and the iPhone had a headstart on Android and Android powered phones.

For hardware, the iPhone was definitely ahead of Android phones, but it was not the first candybar touch-screen phone. That distinction goes to the LG Prada. Also, this was Apple's first phone, vs. some well-established players in the phone industry. For example, some early HTC Android phones were closely related to their Windows Mobile phones, so their hardware development curve wasn't as steep.

I'm not too sure which OS was first. Android was started in 2003 with research into phone interfaces, purchased by Google and started on development to be a full phone OS in 2005, and released in 2008. It's a guess as to when iOS was started. Apple likely didn't start working directly on it until after the 2005 Motorola ROKR fiasco told them they needed to rethink how to do a phone. However, there is good evidence that Apple was researching touch tablets earlier than that, and much of that effort would have gone into the iPhone. End guess: They're probably about the same age.

One reason Apple was able to put out a high-quality OS in two years was that they pulled developers working on OS X to work on it, delaying Leopard by several months. They also held off a third-party developer API for another year. In contrast, Android 1.0 did have the Market when it came out, but overall the OS was pretty rough, even a year later. I had an Android 1.6 (released 2009) phone and played with a friend's original iPhone (updated to 2008). The iPhone easily won all around, except that my phone had 3G.

And now allow me to continue my gripe about support. His iPhone maintained software support until 2010. Three years after introduction of the model it could still officially get the latest OS. My phone got one update six months after it was released (to 2.1), then nothing. Rooted 2.2 and 2.3 will work on the phone, but they just don't feel like rolling out a supported release.