Are there page to page commentaries on difficult philosophical works that explain more simply what's being said so that the average person at least has a fighting chance of knowing what the work says. Where does a person obtain those sorts of commentaries?

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Yes. Actually a great deal of Medieval philosophy (for Jews, Christians, and Muslims) consisted in commentaries (often on Plato and Aristotle), and in modern philosophy there is a famous example of C.D. Broad highly detailed commentary on the work of McTaggart. There are highly detailed modern commentaries on much of Plato, Aristotle, Augustine, Aquinas, Descartes, Locke, Hume, Kant (multiple volumes), Hegel, and Wittgenstein, to name a few. A good university or college library will carry some of these, and you can find the volumes by simply searching the stacks electronically or (as I still prefer) in person. As far as accessibility is concerned, Blackewell, Routledge and other British presses (including Oxford and Cambridge) do have short, very clear introductions to very difficult philosophers (Robert Solomon has a nice short intro to Hegel). But once you have gotten through the introductions, some of the commentaries are very much worthy of patient attention. Broad's on McTaggart is well worth the trouble of slowly working through the texts.

Indeed, there are all kinds of commentaries written on the works of the Great Dead Philosophers, at various levels of sophistication.

But it isn't clear to me why "the average person" would particularly want to read the works of the Great Dead Philosophers -- unless gripped by the idea that those works are somehow full of timeless pearls of wisdom. But that's not a happy idea. Those old works are, of course, very much creatures of their times, responding to intellectual concerns of their times (concerns which might overlap with ours, but which are also very different in subtle and complex ways), and typically bringing to bear all kinds of hidden assumptions of their times. That's why the Great Dead Philosophers can often be so baffling: they can seem to talking about issues that we half-recognize, but often in ways that initially make little sense. And that's why we need the commentaries, to help us see where our predecessors were coming from. (Think for example just how much philosophy over the centuries since the Greeks has been reacting to the science of the day, taking "science" broadly: change the science radically and the problems it gives rise to change radically too.)

The "average person" (meaning, I take it, someone with no knowledge of the area) wouldn't start trying to understand physics by reading the Great Dead Physicists; they'd start with modern textbooks. And likewise the average person wanting to think through some philosophical issues should start with modern textbooks: there are plenty of excellent ones at different levels, which do indeed give their readers more than a "fighting chance".

Of course, working through a selection of such books might inspire you to go on to delve into some aspects of the history of the subject (though many philosophers no more particularly care about the longer-term history than do their physicist colleagues). But that's a different matter. By then you've stopped being an "average person", starting out!

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