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If the alleged pedophile is savvy enough to use Tor, won't he be running his web traffic over SSL, rendering this sort of attack useless?

I'm not 100% certain of this, but I believe even SSL is vulnerable to certain man-in-the-middle attacks when routed through a single point like tor.

A google search returns lots of results, although I'm unsure if any are 'in the wild' exploits.