What you are proposing is a statistically generated version of the Gunning Fog Index (http://en.wikipedia.org/wiki/Gunning_fog_index) or the Flesch–Kincaid test (http://en.wikipedia.org/wiki/Flesch%E2%80%93Kincaid_readabil...).
If I were Google, I'd try that, but I'd also try something like working out percentage deviation from a Markov chain generated from their crawl. A method like that would show that my first sentence is pretty unreadable, while an algorithm based on word complexity would see it as pretty simple.