It probably has to do with Motoblur and the update module working differently on the customized software vs. stock Android. I have the Droid 1 and the girlfriend has the Droid 2, and the 2 does indeed get updates much more easily manually. The 1 had to wait until it was pushed.
Yeah, I guess the thing that was confusing me is simply this: why have a menu option on the Droid 1 if it's totally non-functional? I mean it was always said that the OTA for the Droid 1 was done in waves to prevent a mass-bricking and also to ease the load on the infrastructure. I was wondering what it was about the Droid X/2 where all of a sudden this is no longer a concern?