When looking to order my droid, I saw the same shift in price (I am upgrading with a family plan). Last weekend, Wirefly ran a deal for 19.99 to upgrade as an existing customer. I could not believe it, and jumped. It was legit, and I am playing with the phone as we speak. Perhaps it is worth checking various sites regularly...and jump when the price gets in the range you are looking for?
Oh...and wirefly threw in a bluetooth headset as well...not a big deal, but kind of nice none-the-less.