I am not sure if Gruden truly does love every QB but do you expect the agents of the players to agree to a video that destroys the prospect?
My assumption is that ESPN and the players all make a deal that this session will work well for both parties. Notice how in each video the process is almost identical with Gruden always pointing out only ONE flaw of each player. He talks about all of the great things, throws in something silly (for RT, the singing bit), has them draw on the board, shows one flaw, and then talks about how good they are. I am confident the agent's have negotiated this process. If Gruden kills one of the players, no one will want to be on it (just like QB's don't throw at the combine). If he is always shooting praises, its beneficial for ESPN and the player to be on the show. It is purely a business move and I would not put too much effort into how much Gruden likes the QB's.
With that said, RT has potential to be incredible. I am hoping he learns the pace of the pro game fast.