I'll try to address all your points. Again, I'm not taking sides just posting my concerns.
I really don't plan on using itunes ever! I would look for a jailbreak app that would allow me drag and drop capability.
Don't have to worry about spotty service, I'll be staying on verizon.
I hear you can customize using winterboard.
LTE will be a long time coming where I live, I am not in a big city so I wouldn't really be "wasting" an upgrade discount.
Winterboard customization can't match an Android device... rooted or unrooted. Not even close! LauncherPro does more cosmeticly to your Droid than Winterboard does to an iPhone.
Just to get drag and drop capability you have to jailbreak, install cydia, download the app, and configure. All for something that you can do right out of the box without rooting on an Android device. And if you don't take the proper precautions (backups) you could lose all of your data that you've dragged and dropped. Remember... If your jailbroken iPhone decides to take a dump and you have to reload your OS you'll lose EVERYTHING because you aren't backed up through itunes and your memory is imbedded in your phone as opposed to a fairly isolated SD card.
No matter what, you're chained to iTunes sooner or later.
True, spotty service is an AT&T thing.
The city thing... well. Can't help ya there.
Do what you like, but the grass definitely isn't greener on the other side of the fence. I used the iPhone for 7 months and I've been using Android for over a year. After living with both I can say without a doubt that the iPhone isn't good enough to take me from Android. Been there done that and I'm sticking with what I've got. Literally, I'm a customer for Android to lose, and they haven't done anything to warrant my switching platforms.