The skyfire browser can play *some* flash video, but its far from perfect, and the translation is done by the Skyfire folks, not Flash itself. We're supposed to get full blown Flash by the end of the first half or so, but the truth of that is anyone's guess, though I bet we will get it eventually.
All in all, The Droid and Incredible both run Android 2.1, so the biggest difference is SenseUI and processor speed. I have a Droid and don't have money pouring out of my pockets, so I'm sticking with it until I can at least get a discount, but I'd never trade a 2.1 phone for another phone on 2.1, there's ultimately no upgrade. It's like buying a new computer with all the same specs but a 400mhz faster cpu...there's really no value in that.
If i didnt already have a Droid, I'd certainly lead towards the Incredible, though the remote chance of getting 2.2 faster would certainly factor in my decision to stay Droid, but that's not a guarantee.
As for what's coming out down the road...I honestly dont pay too much attention because they'll all be obsolete by the time I can upgrade anyway. The smartphone obsolescence rate is stupidly fast these days. If you wait to have the best one, you'll wait forever, best to just go with what's available and just know that when its time to upgrade, there'll be some super awesome phones available.
So bottom line, like you'll see in many posts here, is to just go to a VZW store and really try em both out. See if you like Sense over the stock Android UI, if the speed makes a big difference, how much you may like the physical keyboard (I rarely used it at first, and now use it exclusively).