1. I'd say it's simply because they're grand and spectacular. They're on a larger scale and are more impressive---someone stealing a candy bar would rarely make a front-page headline, but someone stealing the Hope Diamond would.
I think Screwtape warns against huge displays of wickedness partially because they are so public. When people come face-to-face with the enormity of what they've done, they're more likely to realise they need help, and therefore more likely to repent and turn to Christ. Sin is a lot harder to ignore when it's huge and public.
Also, I'd say that public sin can be a warning to others. It may make some go, "Glad I'm not like them!" but it can also drive others to Christ, either for salvation or for strengthening. Either way, Screwtape et co. certainly wouldn't want that for the other patients!

2. Screwtape seems pleased enough, but a bit hesitant or uneasy. It's almost as if he knows that Wormwood will inevitably blow it and is trying to somehow keep that from happening. I don't think I really empathise with him though.

3. Perhaps it'd be because the Patient knows that he must do these things, but he also knows he's not doing them as he should. He knows completely leaving them off is wrong, even if he's struggling to do them.

1. Screwtape believes that small sins work best to get souls. However, he says that young tempters like Wormwood want to produce "spectacular wickedness". Why do you think young tempters want to produce "spectacular wickedness"? Why would Screwtape want Wormwood to stay away from things like murder? I agree with Valia that it is largely because they are so big and impressive. The young tempters want to show that they can do "great" things. Also, I would imagine it is more fun for the tempters if the sins are larger. Wormwood gets "drunk" on a war that he had no hand in starting. He could easily get "drunk" on his own success / the evil acts his patient does.

When people come face-to-face with the enormity of what they've done, they're more likely to realise they need help, and therefore more likely to repent and turn to Christ. Sin is a lot harder to ignore when it's huge and public.

I agree. A big crime / sin can awake a sense of "what have I done" and repentance. I could be wrong, but I think I remember something from the Great Divorce about one "ghost" being upset that a murder was in heaven and he wasn't. (the idea being "I wasn't that bad") Small sins are much easier to overlook than big ones. People often have a hard time grasping the idea that any sin is punishable by death in God's eyes. They often believe that if they are "basically a good person" they are fine (i.e. don't need / shouldn't need salvation). By society's standards, they are fine but not by God's.
2. What is Screwtape's attitude in this letter? As a reader, do you empathize with him? He seems to be pleased but cautiously so. He doesn't trust Wormwood and knows what could go wrong. He is trying to anticipate what might go wrong and help Wormwood avoid it. I don't empathize with him.

3. Why might the Patient be reluctant to give up the observances that Wormwood is making increasingly onerous? If he completely stops doing them, he will have to look at the change in himself head on. As long as he is still doing them he doesn't have to come to terms with what has changed. It is easier to push it aside.

1. Screwtape believes that small sins work best to get souls. However, he says that young tempters like Wormwood want to produce "spectacular wickedness". Why do you think young tempters want to produce "spectacular wickedness"? Why would Screwtape want Wormwood to stay away from things like murder?

I think they want to say they have charge of someone who is doing all these horrible things. The bigger the sin the more chance that someone else who is a Christian will notice it and try to help him over come it and get back in the faith. And many murderers have become saved while in death row.

1. Screwtape believes that small sins work best to get souls. However, he says that young tempters like Wormwood want to produce "spectacular wickedness". Why do you think young tempters want to produce "spectacular wickedness"? Why would Screwtape want Wormwood to stay away from things like murder?

Young tempters would want the sins to be more spectacular because they're more "epic". Bigger and better and shinier, in their minds. More bragging rights. Same as catching an enormous fish when going fishing. Screwtape advises against using bigger sins, because he thinks smaller ones will be more effective.

2. What is Screwtape's attitude in this letter? As a reader, do you empathize with him?

I don't think I'd want to empathize with a demon. His attitude is the way it is for much of the book - an attitude of caution and of teaching.

~Riella

1. Screwtape believes that small sins work best to get souls. However, he says that young tempters like Wormwood want to produce "spectacular wickedness". Why do you think young tempters want to produce "spectacular wickedness"? Why would Screwtape want Wormwood to stay away from things like murder?

I agree with both aforementioned theories. The more spectacular the crime, the bigger the bragging rights. Of course if he gets a patient to commit a huge crime, he still has to go about the work of keeping his soul in confusion. -That is hard to do when faced with the reality of death.

2. What is Screwtape's attitude in this letter? As a reader, do you empathize with him? No. I think Screwtapes' attitude here was much the same as in the other letters.

3. Why might the Patient be reluctant to give up the observances that Wormwood is making increasingly onerous? Giving up these observances would send an obvious message that the man isn't practicing Christianity anymore. Screwtape is hoping that even the patient won't realize there has been a change until it is too late.

I agree with both aforementioned theories. The more spectacular the crime, the bigger the bragging rights. Of course if he gets a patient to commit a huge crime, he still has to go about the work of keeping his soul in confusion.

I agree - I suppose that an "inexperienced" tempter would want just those spectacular events with their bragging rights. But Screwtape is trying to tell him that his own enjoyment of the process is not as important as the end result - and the work he still has to do, might be made more difficult because of the spectacular crime. I think the main reason for that is the Patient might then start to think of the horror of what he has done, and start to repent - and that is exactly what Screwtape does not want to happen.