So I ordered my 32gb black wifi ipad2 from B&H on march 31st. These people have the WORST customer service I've ever encountered. I've been calling them for a week now to try and get information on my ipad. They will never tell you when or how much of a shipment they are expecting. They will never tell you where you stand on the wait list. When I ordered my ipad, they told me 2-3 weeks tops. Its been almost 6. When I asked them to upgrade my shipping they flat out said NO. I would never order from them. I've been calling around to see if anyone else has them in stock and by far J&R has been the most helpful. They tell you exactly when and how much of a stock they'll be getting.
Shipping upgrades cost companies money and reduce their profit margins. So they have less money to pay the people we're harassing on the phones. It doesn't hurt to ask and it's nice if they give you one, but are you really entitled to a shipping upgrade?