General question: Given a dartboard of unit radius, what's the probability that a dart randomly lands within a circle of radius 1/3 centered inside the dartboard?
Standard answer: The dart is thrown such that it hits each point with equal likelihood. The probability that it lands within the inner circle is the ratio of the areas of the two circles, which is 1/9.
Other formulation: Suppose that the dart is thrown directly at the center of the dartboard, but wind comes from a random direction. For any wind direction, the velocity of the wind pushes the dart some distance from the center of the dartboard to its perimeter, with each distance being equally likely. Each wind vector is equally likely and, for each vector, each distance is equally likely. The probability of being less than 1/3 units from the center of the dartboard is 1/3.
The definition of randomness is different for each formulation. In the standard answer, a random vector is chosen from the set ${(x,y)\colon \; x^2+y^2 \leq 1}$ and we ask the probability that $x^2 + y^2 \leq \frac{1}{9}$. In the other formulation, a random vector is chosen ${(x,y)\colon \; x^2+y^2 = 1}$ and, on this vector, a distance $d$ is chosen uniformly on $[0,1]$. We ask the probability that $d\leq\frac{1}{3}$.
I understand the math of solving this problem, but I don't understand intuitively why these different conceptions of randomness give two different answers. It seems that both are valid means for answering the general question. Intuitively, why do they give different answers?