IOS is not lockdown city you can jailbreak it quite easy, for such a long post you sure did screw the pooch at the end, makes me question your actual use of an iphone.
Maybe you just missed this part in my long post... " I didn't like the iPhone because I couldn't tweak it without a jailbreak and jailbreak just isn't that much better."
I'm a geek... I like to really tweak my phones and mess around with them. iPhone you can't do that... not compared to what you can do with the Android and the pantload of custom ROMs and addons you can do once you root your phone. Jailbreak gets you access to Cydia which is another App store. And there are some cool tweaks there for the iPhone... but not to the level you can get with Android.
I've done 18 months with each phone except the iPhone 4S. The 4S I gave to my daughter and bought the S3 because being on the Moto Droid X (not a fantastic phone, but an Android nonetheless) spoiled my inner child who likes to break things and figure out how I blew it up.
That being said... one other problem... if your friends and family have iPhones and you do iMessage group texting... it can suck transitioning to Android. Need to get a 3rd party App to support the MMS implementation iPhone does with their group messaging and its not always great.
LOTS of things to consider... I don't envy you Dave.
Play with the phones... make sure they have some kind of return policy where you can exchange if you don't like it. Think about all that is important to you in a smart phone... and then go from there. And have a few stogies while you ponder the direction you head.
