No, no, no. Three problems, one in the analogy and two in the probabilities.

First, an individual particle can briefly exceeed the speed of light; the *group* velocity cannot. Go read up on Cerenkov radiation: It's the blue glow created by (IIRC) neutrons briefly breaking through c, then slowing down. The decrease in energy registers as emitted blue light.

Second: conditional probabilities are not necessarily given by a ratio of densities. You're conditioning on (or working with) events of measure-zero. These puzzlers are why measure theory exists -- to step around the seeming 'inconsistencies'.

Third: The probability of a probability is superfluous. Probabilities are (thanks to Kolmogorov) just the expectation of indicator variables. Thus P(P(*)=1) = E(I(E(I(*))=1)) = 0 or 1; the randomness is all eliminated by the inside expectation.

Leave the musings on probabilities to the statisticians; they've already thought about these supposed paradoxes.