Anyway, this Scientific American article offers some speculations about why most of us don't intuitively understand probabilities, and perhaps sheds some light on why problems like those mentioned above can be so bewildering. The article's argument boils down to the idea that we live in the "now", that our brains are hardwired to easily handle only a small number of event occurrences. When we come up against large sets of values, we have a tendency to focus in on its subsets or singular values, which obscures the connections that exist between the set's members.
A very interesting (and short) read...