This program models his suggestion that, were a monkey allowed to type random letters, he would produce a work of Shakespeare very quickly if letters he happened to type in the right places were preserved with each attempt.
"Very quickly"? Highly doubtful.
Who or what intelligence determines the "right places" and who or what intelligence does the preserving?
Dawkins is a clever atheist ideologue, nothing more, and he has risen to prominence because he is an atheist, not because he has anything useful to say about Evolution. He is making an effective argument here for Intelligent Design.
Not really - empirically verifiable. Here's a Java version of Dawkins's simulation, slightly modified. Stick in a phrase, see how long it takes to generate it by cumulative evolution.
Who or what intelligence determines the "right places" and who or what intelligence does the preserving?
The shortcomings of the analogy are not the shortcomings of evolution - evolution is not goal-driven (teleological), as the Shakespeare example is. However, if you understand that Dawkins is trying to illustrate how adaptive traits are passed on, rather than scrapped - as this article would have us believe - then the analogy is still a useful illustration.