Question: Why did Simon set up so many riddles for McClane? Wouldn't he expect McClane to be killed in Harlem? Simon later says to Zeus on the phone: "My only problem is that I went to some trouble preparing that game for McClane. You interfered with a well-laid plan." What exactly was the plan, if he didn't expect anyone (Zeus) to help, or any gangs, etc. to take offense and kill McClane?
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Chosen answer: Simon Gruber was deliberately seeking prolonged, torturous revenge against John McClane for killing Hans Gruber (Simon's brother) in the first movie. Gruber expected McClane to suffer through the Harlem humiliation and suffer through subsequent, carefully-orchestrated obstacles that McClane may or may not have survived. Gruber deviously intertwined his revenge plan with several spectacular bomb diversions across the city (drawing attention away from Gruber's gigantic gold heist). However, in the end, Gruber misjudged the full extent of McClane's tenacity and resourcefulness, just as his brother did.