1984 is a dark novel so it generally does not contain any positive themes.
Luck is inadequate for Winston because he ends up getting caught committing crimes against the Party even though he painstakingly took his time to avoid getting caught. I don't really think it was about luck, the Party simply tried much harder to catch Winston, than he did to avoid it.
Cunning in the novel is inadequate mostly in Julia. She is young and fearless and it causes her to be much less careful. She almost flaunts her relationship and her past sexual promiscuity because she wants the Party to know her feelings. She also lacks cunning because she cares little about how the works on the whole, she only has disdain for the rules, but not the purpose or the "why".
Winston is representative of the lack of boldness in the novel. He lives in utter fear and in doing so is terrified to do much in the face of the Party. He does do more than most, but he isn't what I would call bold, he takes his time and thinks about all the ramifications before he does something. He had the journal for over a week just thinking about it before he ever cracked the cover to write in it. He thinks about murdering Julia when he thinks she is a member of the thought police, but thinks so long that by the time he decides anything she's gone. Julia makes the first move. He rarely voices his opinion, and that is largely the fault of the Party's conditioning.
This could be a good one for the Discussion Board too.