@steephie, I love your question and I love the connection to game theory. As it happens, I'm an electrical engineering PhD student studying game theory. :) So maybe I can fumble around with this.
I think you're getting yourself into trouble by talking about electrical resistances and individual electrons in the same sentence. Individual electrons are difficult to predict, control, and even describe. They move around randomly and can't be individually tracked (because of that damn Heisenberg principle). This is what abgemacht was talking about when he said "electrons actually travel very short distances...."
But physicists came up with a nice work-around: since there are billions of electrons in a wire, we can describe their *average* motion very precisely with the notion of electrical currents (measured in "Amperes"). An electrical current is defined (in very broad terms) as a net motion of electrons. Suppose you have two currents: A) 1 electron moving at 1 m/s, and B) 2 electrons moving at 0.5 m/s. Which has more amperes of current? It's a trick question: both have the same number of amperes! (footnote to the pedantic: my units are wonky, and require an uninformative correction factor. Sorry. The concepts are still correct.)
So here's where the answer to your question starts to emerge: Because current is just a measure of average electron motion, we can do something kind of funky: we can describe the above current as 0.5 electrons moving at 2 m/s. Since a current is just an average, fractional electrons are fine. We're not literally saying that the electron is cut in half; we're saying that for all intents and purposes, we might as well describe the electron as being cut in half.
Now let's think about your single-electron experiment in an actual circuit. The quick, dirty answer is that there's no such thing as a single-electron current in a wire, because a current is defined (roughly) as the average motion of *all* electrons in a wire. If you took a single electron and somehow injected it into the circuit and tried to track it, before long it would collide or interact with other stuff in the wire and its motion would average out to be a very very very small electrical current, which would split nicely between your two circuit branches according to the rules of a current divider.
So what's the point of all that? I think I'm trying to get across the idea that your original question is not well-posed: you're asking a question about the behavior of individual electrons, but you're asking it in terms of average electron motion (by referring to resistances and circuits). Thus, the answers are going to sound weird and un-intuitive. Let me know which parts of my answer are the most confusing. :)