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These phones are different on the inside and outside, although the overall idea is the same the exterior has an updated shape which will make Droid 1 snap-on cases unusable. Holsters and pouches might work and possibly the battery from the D1, also it is not said if the D2 has MotoBlur or not which to some people is a big set back. The D2 ships with a tiny 8gb sd card, so if you are upgrading from your Original Droid you will have to switch those out, and as you said the keyboard is new and refined but personally I have become used to my Droid keypad. The new voice search key on the D2 physical keypad is a nice bonus but the worst is they have switched the soft keys at the bottom of the screen all around making it very confusing for an Original Droid owner to navigate around
Definitely I don't think this is a device worth upgrading to if you already have the Original Droid...wait it out and see what the holidays bring
The lip won't matter. I have the Droid home dock and there is no part that sticks into the lip area, so as long as the length and thickness and position of the micro USB are the same, the Droid 2 will fit the docks. The fact that the screen half is longer than on the Droid will make no difference. I don't know about the car dock.