I think what makes the Droid a capable phone is its specs - they outshine the Iphone in every regard. But there is probably a new iphone that basically must overcome the droid in terms of specs, and even some of the upcoming ANDROID based phones.
Snapdragon CPU based (Android) phones (1ghz cpu, being released on major carriers soon)
There is some rumor Google is dinking around with maybe doing their OWN phone, but I think its unlikely given how Google just doesn't do hardware, they do software. They had a LOT to do with the Droid. The Droid is the next generation, or next step for the Android OS
The Android OS is showing more promise and Android based phones are expected to surpass Iphones in like 2011 if I recall.
I don't think the GUI is hard to use, and I think the phone is just very capable an most importantly the service is just killer. It works really well in like 9 / 10 spots in SLC it seems like. 3g coverage at all the resorts I've been to.
The Android OS is the big underlying thing that people are discussing here, the OS is kind of like Windows now in the sense of you can just download 1372 bull shit apps, clutter your screen with a fuckin ton of widgets and gadgets and icons, and have like your phone doing 3-4-5 things at once. You can install GUI's or in other words change the physical appearance of the desktop. To say the SenseUI GUI, or MotoBlur GUI. If im not mistaken, even an Iphone GUI.
The usability and speed of the phone is increasing with every update. Android 2.0.1 was a big upgrade I think. Came out just before Christmas and it fucking really made the phone speedy.
Verizon has a 30 day return thing though, buy it, hate it, return it.
There are always new phones coming out, just like computer hardware, so deciding what to buy is basically like what do I buy now. Becuase you never ask yourself hmm what should i sign on to for 2 years today? So you basically need a phone in the next week, not the next quarter of a year. Or you wouldn't be talking about this I don't think.
If there is news of a new killer phone....you have 30 days to return that bitch and say i'll wait to fuckin be in a new contract.
The phones apps are limited by your wallet. The cool shit costs money, but there a ton of simple ones out and some even really useful ones that are free in fact.
You buy an Android based phone and you are investing Googles success with these phones. You purchasing a phone will in turn make my Google experience better as the phone surpasses the Iphone in terms of developers working on apps, apps in the wild for users to download, and most important...choices
Motorola, Samsung and HTC all make Android based phones. You don't have to have a Motorola Droid. In fact the Samsung U939 or something on T-Mobile looks impressive specs wise, but I haven't played with it.
Ultimately the more power under the hood the more you will be able to do with your phone as the smartphone market continues to have more advanced apps / games that demand more resources. So buy as much as you can afford in that regard. The phone cost is like 2% of the cost of the plan over 2 years......and then you will never live without 3G again because you fucking love a smartphone.