It's really a preference issue. The iPhone is a lot more intuitive and a lot of the apps are really polished, but there are quite a few limitations I do not care for. I don't like the fact that jailbreaking makes updating firmware such a pain neither. I will say that there are quite a few things out there like jailbreakme and [color]sn0w (redsn0w, yellowsn0w, etc) that make the process very simple. Android has a lot more variety, so that's a positive and a negative. It's a problem when you deal with apps that do not work as well on certain devices as they do for others, but they are highly customizable and there are a lot of ROMs out there to fit your flavor.
I have to deal with both types of phones on a regular basis at work and though I will see more Android related questions they tend to be minor, but when I get an iPhone problem it usually is some major problem with their firmware updates or problems they created jailbreaking the phone on their own. But I find that to be rather consistent with X product vs Apple product. I get frequent minor problems with product X but when I'm troubleshooting an Apple product there seems to be something seriously wrong--but that is a rant for another time.
The iPhone has a huge advantage in that it's an iPod, the controls are well known and very user friendly. And it would hard to ignore the abundance of devices that you can simply plug your iPhone into.
For me, one of the biggest pluses for Android is expandable memory. I like the idea I can pop in SD cards to have more memory instead of being stuck with the memory included in my phone. That and the plethora of apps such as DSP manager (and for those with supported phones, Voodoo Control) and all the great music players.
Though I voted for Android, this is a preference thing. I like to customize my stuff and don't care for the way the iPhone does things. But your miles may vary.
