"Verizon upgrades" is a process, not an event. They're rolling out LTE test sites next year, and if all goes well, it gets deployed on a larger scale, and gradually, the average person may have some change of being near it.
Look at how Sprint did this with their WiMax (they're the only major telecom company going to WiMax rather than LTE for 4G).. they were in Baltimore last year. Now they're in five additional cities, including Philadelphia (where I work), partnered with Clear. But the Clear people were having trouble setting up demos, due to spotty coverage.
I work in communications these days (digital radio design, optimized for robotics), so I have been following this for awhile now. I had no problem buying the DROID at this point. If Verizon is very, very aggressive (and they're likely to be, given their win of the big 700MHz band chunk), it'll still be some time before LTE is a regularly seen thing. I'm fairly sure I'll be able to wait until 2012 and the DROID 2 or 4G or whatever. Just as important... that 4GB of internal memory, 1.6GHz Cortex CPU, and microSDXC slot (come with 32GB card).... and increased run time.
At least, let's hope that DROID is a big success, but unlike Apple, Motorola really boosts the capabilities from rev to rev, rather than just tiny little tweaks. They'll have to.. there's real competition in the Android market. As with the PC, we users benefit from this.