I guess the questions and theories abound.
We do know this:
For a phone being compared to every other new thing out there, the Moto Droid is still being shown more often in advertising than any other, bar the incredible. We have seen NEW Droid commericals, and these have to go past moto and VZW.
It still warrants an upgrade due to the time constraints mentioned before, I myself have 1.5 or so before upgrade time.
As to when, it is possible that as Hooky's source indicated, that it's in the hands of testers right now. With everything said I can go with that 50%.
It begs the question: Could VZW/Moto get the Droid Tested on 2.2 with no leaks?
N1 gets it first because Google doesn't have to pass it thru anyone, just send it out to the units.
Now, some rumors floating around say that VZW wouldn't be involved in updates. Possible? Perhaps. Tethering questions abound, don't know if other changes in 2.1 to 2.2 require any "testing" of network performance, I would think so but you get my point, if it isn't changing basebands, etc... (If I'm wrong, let me know, NBD).
My feeling towards early June go like this:
1. Getting it out to a popular phone that is still pushed hard on TV, etc, and with a good segment of the population BEFORE the Apple Conference is a win for both VZW and Moto.
2. Add to that Adobe making public statements about flash being on the moto Droid, and needing 2.2 as a requirement (Didn't this change? Thought 2.1 was going to be it....) makes it a DEFINATE that the moto Droid would get the update.
Kinda locks it in eh? Just as to when you go back to #1.
I would like to think that it can be implemented now by VZW, like the palm with a 5Gb cap, and then they can change it later on to charge, we know that is going to happen, but it would be nice to be wrong there.
It's going to be a long June isn't it?