Interesting question. Originally, I thought that we can specify a random circle on the plane by picking a random coordinate for the center, and then uniformly sample a radius from the interval (0, inf). That didn't work out so well in computing the probability of containing the origin.
Here's another way to construct the random circle. Uniformly sample 3 points on the plane, and use it to construct the circle. All circles can be uniquely determined by 3 points. Since the constructed circle will also include the triangle specified by the 3 points, the chance that the circle include the origin is greater than that of the triangle, which we know is 1/4.
But here's another way to construct the random circle. Uniformly sample 3 points on the plane, and use it to construct a triangle. Now, we construct the circle as the biggest circle that can fit inside the triangle we just made. Since the constructed triangle is smaller than the triangle, the chance that the circle contains the origin is less than 1/4. In this example and the one immediately above, we could estimate the chance of the circle containing the origin by finding the ratio of the area between the circle and the triangle.
The 3 methods above equates to different density distribution for the circle on a plane. There are many other ways of specifying a random circle on the plane, though.