There has never been a single Android phone made by a normal carrier (Samsung, HTC, Sony Ericson, etc.) that has missed all software updates. Since you seem to want to mention iPhone, iOS 5 doesn't really support old phones either. 2G/3G are out entirely, 3GS is horribly gimped, and even 4 doesn't get a couple features (namely Siri).
Phones are shipping with 2.3 for the most part, unless you're getting an extremely old/extremely cheap phone running 2.2. 3.0 is not a phone version of Android, no phone runs it. 4.0 isn't even OUT yet, and when it IS out, it will only be on the Galaxy Nexus this year.
Your HTC Hero wouldn't gain a thing from 2.3. Cyanogen has a hacked version for it, and it's not even worth the time. It's what, 3 years old now? Christ sake, move on. The 3GS runs like crap on iOS5 as well, and as I mentioned above, misses tons of features. Would it make you happy if HTC gave you Android 4.0, but removed 90% of what makes it Android 4.0? No, of course you wouldn't, because that's little more than a lie. Also, the 3GS at least has the benefit of having a newer processor. The HTC Hero actually is hardware equals with the iPhone 3G, aka, close to four years old.
No, they never admitted such a thing. It WAS meant to help tablets get moving, since yes putting 2.3 on a tablet is dumb. However, Google HAS announced that as far as Android is concerned, any device running 2.3 or above is capable of running 4.0.
Huge amount, not really. And new phones actually keep damn good pace. No, it's not iPhone fluid, but it's not slow as **** as your Hero probably is. Your Hero sucks, stop blaming Android. Also, oh no, carriers stick crap on the phone you don't want! It's not like Apple does this themselves, cramming Newstand, iMessage, Reminders, and all sorts of other crap I'll never use on me.
OH GOD, THERE'S A WIDGET WITH A CLOCK ON THERE! Who cares? That's Android, if you don't like it, change it. You know this very well.
Finally, I find it amusing you're flying right into an iPhone4S. Almost every complaint about Android is valid for iPhone, and you think iPhone is perfect? Hate to break it to you, it isn't. iOS has plenty of flaws under its belt. Apps crashing, crappy app store quality control, absolutely horrendous lockdown of the system (seriously, still no file management whatsoever), etc. Multitasking is a joke, the screen is tiny (Yeah, I went there), etc.
Seriously, what is the problem with a larger screen? If it fits in your pocket, what is the problem? This is something even iPhone-friendly reviewers have been discovering lately. No, you do not need some 5" beast, but Android has OPTIONS. The additional screen size makes things easier to read, it makes it far easier to type, etc. In addition, almost every Android phone isn't made out of front-to-back glass, just asking for it to be shattered.
Frankly, your ENTIRE argument was boiled down to three things:
1. Your outdated piece of crap HTC Hero is an outdated piece of crap. Welcome to technology, your iPhone will be irrelevant next year.
2. Android OS versions are non-consistent. This would probably be a critical thing if we were all still waiting on Froyo. But I dare you to name one single improvement in Gingerbread without Googling. Even still, almost every phone you can buy is running 2.3, which is the latest released version. 4.0 is coming out soon, and if you are worried about it being outdated so easily, get a frickin' Nexus phone of some sort.
3. Android has MASSIVE SCREENS and DOUBLE CLOCKS! Seriously? I can't fathom that this is actually a problem for you.