I also had an iPhone, and I hated iTunes... the clunky interface, so slow to sync, etc. The only thing I liked was that it was dead simple to keep it backed up. But like I said before, it's really not critical to keep an Android phone backed up on the computer because all your stuff is automatically in the Google cloud.
We're getting the latest ICS update soon, but wow, the OS came out in fall of last year, and we don't have it yet. Google will be introducing the next version of Android soon, and most phones still don't have ICS. This is the main/only thing I don't like with Android. I wish all capable phones would get the latest OS as soon as it's released by Google.
Anyway, updating, as I understand, should be painless. It will come over the air, so you don't need to plug it in. We will probably get a notification that it's available, and in a click or 2 it should download and install. This is much better than the iPhone, but I think the latest iOS now also finally has OTA updates like Android.