Well, here is how I look at it...
As a Droid 1 User, I don't see the point in going to Droid 2 for a few reasons:
1) I bought a Droid 1 in November... not even a Year has gone by and my phone works fine.
2) Still under current 2 year contract. Again, not even a year has gone by and I just can't justify switching to a newer version so quickly for costs.
3) Not much of a 'gain'. The 'gains' for it doesn't justify the cost for me. Yes, it has improvements over the original, but then again, I am one who tends to run things to the ground unless I need a newer item that outweighs what I have or the one I have is pretty much dead.
4) I'm no custom mod fan... I tweak my computer a little, do a little customization, but I tend to run things at stock level because I'm one of those people who don't want to mess with things unless I have backups. Given the expense of the Droid initially, I avoid rooting or hacking mine because I am a simple user for it and the stock model works fine, even though I am a tech type personality.
I feel that the Droid 2 is not doing well mostly due to the fact that the Droid is now hitting saturation to a degree. Others are just also gravitating to their Android counterparts in the services that they are on, now knowing that the Droid uses Android OS and there are those alternatives with their carriers that still provide a decent service for them.
I also feel that the new models are just coming out too soon. With Motorola pushing out Droid X and then Droid 2 within 1 year of the initial Droid release... Of course it won't do nearly as well, again, due to saturation of the Motorola Droid product line, it's worse than a car, in my opinion.
At this time, if I want to consider a new droid phone, it would be for two reasons:
1) My current droid suffers serious failure (be it melts down, I break it or so forth)
2) The next gen Droid supported by the 4G network, provided the 4G network provided sufficient needs. By then, there should have been even more improvements in Android OS as well as other things to make it worthwhile to get it.