Chapters III & IV

1. O'Brien is a member of the Thought Police, do you think he can actually read Winston's mind? Did O'Brien actually permeate Winston's dream all those years ago? Explain your answer.

I don't think O'Brien can actually read Winston's mind, I think it's just that since he was in the same exact situation as Winston is now, O'Brien has had the same thoughts that Winston is having now.
Sometimes we have dreams that kind of foreshadow something that's going to happen later on, but what happens in the dream doesn't have to be exact as what will actually happen, it could be something like an indirect dream, in the dream something happens and you might conclude something out of it, but when it happens it's slightly different or turns out with a different meaning to the one you concluded at first. So this is probably what happened to Winston, he had a dream with O'Brien where he was telling Winston that they would meet in a place where there is no darkness, Winston as well as us, thought that this place where there's no darkness meant that the Party would be attacked and destroyed and "light", freedom in every sense, would finally be given back. But really what this meant was the Ministry of Love, this was just a misinterpretation of the dream.

2. O'Brien has made it clear the Party will kill Winston at some point. We know they want folks to understand and believe before they die, but.....if they are not going to release these people back into society, why do they bother with the time and expense of the torture and "rehabilitation"?

O'Brien said that if they're going to kill an individual, they want them to die with the correct and appropriate feeling towards the Party, the feeling of love and loyalty to BB. Die with a good brain to the Party.

3. What's in Room 101?   The most impressive answers will be those consisting of just one sentence.

I'm really not sure what Room 101 is, but I think it has to do with fear, because the last step is to learn how to love BB. A kind of fear that confuses feelings, love and hate. Confuses that fear they have forced into you and makes you think you love him instead. Just like the other people, I don't think they love BB, during the Two Minute hate ceremony people go insane when BB's picture comes up, they make it seem like they have this enormeous and endless love for him, but I think that their feelings are confused from hate to love. So in Room 101 they probably have this strategy to make your fear grow so intense that it actually makes you think you love him.