Riddler with prep-time Vs. Black Widow

The Riddler (New Earth version with standard resources to start), has been hired to either kill or capture Black Widow using any means or strategies he can conceive of.

• Round 1: Riddler has 3 days of prep time
• Round 2: Riddler has a week of prep time
• Round 3: Riddler has 3 weeks of prep time
• Round 4: Riddler has 2 months of prep time
• Round 5: Riddler has 5 months of prep time
• Bonus Round: Riddler has indefinite prep time, but Black Widow knows he's gunning for her, and so is actively looking for him. So it's basically a race against the clock.

Can Riddler succeed?

Vs.

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@professorrespect

@ashrym

@shroudofsorrow:

Unless i am missing something vital here in favour of BW, doesn't riddler fairly convincingly kill her every time? He's got some good feats of being both stealthy and preppy with bombs etc, and given his prep time and direct orders, he's not underestimate her and mess about as he does with Bats

@cergic: Riddler's good with prep, but he isn't unbeatable. He usually plans his crimes in advance but has been thwarted by Batman before. But then, I did this one because I was hoping for some arguments / insight for one or the other.

Bump