Not sure if my reply is too late.. but here is what I've got for an opinion so far...
I had an iPhone 3G (not the latest one), and it was really cool. In my honest opinion, the iPhone beats the Droid (and any android phone UI) for one main reason.. simplicity, broken down into two areas. The iPhone has a purely consistent UI design. From the moment you log in, it is all, and only all icons. That is it. So, for mom and pop, this is ideal. It's really easy to use. BUT.. and I honestly did NOT think I was going to say this... for MORE users these days (than say 5 years ago or so), I think the DROID (and android UI) is a LOT more fun! The iPhone may have the edge on the rounded looks, but to me the UI in Android phones allows you to enjoy the phone more. I think it was Android 1.6 that brought in the widget thing.. that is genious. I am not too happy I only have 3 screens to use them on, as I filled all 3 up very quickly. But, that said, being able to put a clock, power bar, facebook stats widget, calendar widget, and some favorite icons all within a single flick (if they aren't ont he main home page), is brilliant. The fact that you can customize the home pages so much is even more fun, and to me what a lot more teens/20 somethings are going to probably migrate to Android phones for. There is just SO much more you can do to the UI interface on the Android phones. I compare it to MySpace... you see how many teens/kids jumped on MySpace and loaded up their page with their favorite dooda's? Well, to me that is a big bonus for Android UI.. it allows kids/teens (and all the rest of us too) to customize it how we like. I don't know for sure as I've only owned an Android phone for 2 days now, but I think there are apps that bring even more home screens and customizations.. I just came across some "themes" or something that are like .99 each for an app you buy called aHome or something?
As for the keyboard.. having daily swearing sessions on the iPhone virtual keyboard for constantly screwing up my typing.. UGH! I was so pissed. So, let me tell you what a pleasant surprise the Droid phone's virtual keyboard is! I've read a lot of reviews saying it wasn't so good, or that the auto-correct wasn't so good. Well, true, the auto-correct isn't as good, but I seldom fat finger two keys on the Droid virtual keyboard. I am extremely impressed with the accuracy of the screen! As for the physical keyboard, well I think it will be fine for kids, but I have big hands and fingers, so I do tend to have a bit of trouble with it. However, it is better than I thought it would be. Coming from an iPhone, with no keyboard, I find it to be fine for most things. I would rather have seen some spacing between the keys tho.. even if that meant they were a little smaller. For the most part, I've barely used it with the accuracy of the virtual keyboard.
I've only experienced one issue, which showed up twice and so far not again. I put my phone down after bringing it home Friday, and it went into a sleep mode I guess? I couldn't get it out. I looked online, apparently the TMobile G1 had a similar issue.. at least some users did. I had to pull the battery out and back in to get it to come on. I don't know if there is some special way to physically reset the phone, like CTRL-ALT-DEL lol, but I tried every key, combos, long presses, etc..nothing. The next morning when I woke up..same thing. Since then, it's not happened tho. I am hoping it wont show up again.
As a java developer and one learning android development, I had a bit of a time getting the Droid to show up on my Linux development box. Thankfully I came across a post that explained what to do specifically for the Droid and am now able to deploy my apps onto it. I suspected tho it being so new that it may be a short while before it works for this purpose, so it was nice to see it actually work on day 1.
Overall, I gotta be honest, as a techie/developer, I love the Droid WAY more than the iPhone. In fact, after having the Droid, there is something I noticed about the iPhone that really bugs me (my wife still has hers). There is no back button. When you are in an app, you have to press the only button iPhone has, the home button, and it takes you back out of the app. I suppose this is because the iPhone can only run a single app, which makes sense. But it is VERY nice to be able to have those 4 buttons that take you home, back you up a step, or go do a search, as well as a menu button that is context sensitive. I believe the rumor is the next version of the iPhone besides being more powerful, will bring in mult-threaded apps so that more than one can run at a time. But until then, the Android phones have a huge advantage in this respect and in my opinion, allows more flexible options when running apps and navigating in general. It is indeed odd tho that there is no talk/hangup buttons. I see why they did it sort of.. but I would love to have those still.
Oh..the video recording is pretty decent. I did not know there was going to be an update in December.. anyone got a URL for info leading to it? I'd love to know how I can stay atop of upcoming updates, what will be in them, etc. I'll look around the Android forums some more to see if I can find anything about that.
I'd honestly say, get the phone now. Start enjoying it now. Learn it, etc. By the time the updates come and fix any issues, you'll already know your way around the phone.