As OP says, he "use[s the] expected values throughout this post,"—I don't think average/expected value is really an accurate way to make decisions about non-averaged decisions. Primarily, if you always choose the more expensive thing to save time, justifying because your average value makes it worth it, you will inevitably end up "saving" time that is useless; therefore, you'll end up—on average—spending more money than the value you create.
Does anyone else feel this way/think I'm crazy for thinking this?