Should I buy the Iphone? (again)

Yes, I bought the phone on the day it came out. Loved It. Returned it due to cold feet and the massive expense (599 + 175 cancellation fee-- Verizon).. and the "no insurance".
Now time has passed, the phone has proven worthy.. and dropped in price. I am tempted to go get one again, and keep it this time.
Now, I wonder if I should wait till Christmas or something for the next "upgrade"..
Any thoughts on waiting? Or advice on possible new versions?
Thanks

I think the danger is in approaching the question from the wrong angle. Considering it from the standpoint of what the iPhone can (or can't) do in comparison to other devices isn't the best way to analyze the matter. In every case there are comparative products offering more or less features, at greater or lesser prices, that's the nature of the marketplace. Applying your set of criteria to someone else's choice would be the equivalent of telling a prospective car buyer that you wouldn't get the SUV being considered because you can't carry a cow in it.
The only valid approach is to consider what the individual actually needs first, and then basing a choice on what product meets that need. Thus, while the iPhone lacks a lot of features other cellphones have, if the individual doesn't want those other features, but does want what the iPhone has, the iPhone is the perfect choice regardless of what it doesn't have.
For example, you list poor support for Outlook. True. Not much of a problem however for those who don't use Outlook, or have no need for the comparative sophistication of ActiveSync. You say it has no external memory option. True. Of course 8Gb is somewhat larger than the memory in most other cellphones, so external memory isn't much of a problem in that sense. No games... True. Not an issue to those who don't want to play games.
The point isn't that these lacking features aren't important, because to those who want these things they are important. However, to those who don't, they aren't.
When buying anything, the consumer invariably has to make compromises. It's a rare thing that any manufacturer makes a product that fits the exact need of the individual. So the buying process almost always involves the individual in making compromises about which features matter and which don't. In the cellphone market, there are any number of little devices offering tiny keyboards, cramped screens, poor interfaces, multitudinous features and levels of sophistication which, quite frankly not only would have seemed impossible just a few years ago, but which are often hard to use or place the device in a market segment which is increasingly narrowing to the technically minded consumer. Nothing wrong with that if that's what the consumers in that market want. However, what about the rest of us? Consumers who want something more flexible than a simple cellphone, more capable, but who don't want the complication of the typical UI such devices have, or the balance of the extended feature set they will never use?
Up until the iPhone came out, that sector of the market was really not served with any device at all, and for consumers in that market segment, the iPhone is a far better choice than any of the other so-called smartphones - not because it is better but because for them , it is.
Ultimately, there will never be a perfect cellphone until each of us can design and build our own. Personally, I've tried the kind of smartphones you describe and I've found them universally awful. Too fiddly, poor interface, feature set wholly unsuited to my needs - too much attention to the notion of being all things to all people and as a result being just short of really good at any of the things they could do. I'm clearly not in the market segment they are designed to appeal to. By comparison, the iPhone is a wonderful thing. It's superb at what it does, and what it does is fit my needs far more closely than anything else I've tried. That makes it as right for me as it's wrong for you. That's exactly how it should be, because we each have different needs and wants and different products are needed to serve our individual purposes.

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