Agree regarding Sturridge, I did say that Chelses was thin in the forward sector, so unless they bought/loaned somebody, it would not have made sense to them. They were wise enough to make sure they had a cover first before loaning out not as us.
With regards to Dempsey, I don't agree if the manager thought he could make a difference, 6m is not that much for his qualities as re-sale value comes in the picture only if you want to sell at a profit. If you take a player like say Allen for 15m on a 5 year contract, you should not think about re-selling especially if he is good. You would rather wish to keep him for as much as he can play, re-newing his contract so that he can help you win trophies / champions league place. Now if you can get Allen on a 5 year contract, he would be amortised by 3 million yearly in your books. That would be the exact amortisation in your books for Dempsey if you could get 2 good years from him, which is totally possible. If Fergie or the Glazers were thinking in re-sale value terms, they would not have bought RVP. They rather thought about winning the league / champions league that would increase the value of United and can get them better sponsorship contracts and sell more merchandise.
Now with regards to Caroll, probably BR did not want him, but he should have said you get me somebody first then you send him on loan. He might have said, I don't want him, ship him out as soon as you can and get me somebody else. Our life is all about choices we make, they say. I agree with you that BR does not rate Caroll at all and his priority was anybody but Caroll. Time will tell whether he made the right choice, but, definitely for me it's not looking good.