This semester I’ve had ideal circumstances for teaching Hegel: a very motivated student and a one-on-one setting. My ultimate goal, however, would be to teach a proper course, and I imagine (based on my experience teaching Heidegger) that such a course would be pretty full at Shimer. Here are some of my thoughts on how to organize that.
First, I think it’s absolutely necessary to pair it with Hyppolite’s Genesis and Structure. Hegel infamously refuses to cite his sources, and simply providing that context (which includes many texts that Shimer students would have actually read) is invaluable. Hyppolite has his own reading, of course, but so far it seems that he has kept his axes relatively unground. For any given day, then, I’d assign a certain segment of the Phenomenology and the parallel text in Hyppolite.
Second, I don’t think they need to do everything. For the segment on “Observing Reason” (which I had us go through much too slowly this semester, due to my relative unfamiliarity with those sections), I might assign Hyppolite and tell them to scan over the actual Hegel — they should know what goes on and how it recapitulates previous movements from a new perspective, etc., but they can probably get by with just a description. I would also omit “Religion” and — perhaps more controversially — both “Absolute Knowledge” and the Preface. (In any event, I would save the Preface for last if there turned out to be room.) By my math, this would make it possible to do less than 10 pages of Hegel per session on average (assuming three days a week). Even paired with the Hyppolite, the reading load would still be light compared to the Shimer average (30 pages per sesion).
Finally, I think this approach would leave me room for some further secondary essays, where I could incorporate a range of perspectives (particularly feminist and black perspectives) on one of the ultimate Dead White Males.
An und für sich 
I think looking at the Preface later is a good idea, but I wouldn’t want to skip it entirely: too much is going on there to just omit it. Reading it last is probably fine; that’s when it was written anyway. “Religion” I think is probably a fine section to trim for time, given its size. I don’t see why you’d cut out “Absolute Knowledge”, though; even if you don’t want to spend much time talking about it, it’s short and not terribly difficult (as far as PhG goes).
Are you using the Pinkard translation? I like it quite a bit more than the Miller, and the facing German is really convenient. (It’s a pity it’ll never get published, I’d love to have it in proper book form with decent binding etc.)
I’ve stuck with the Miller, mainly because it’s a proper book. And people tell me that, while not ideal, it’s basically good enough.
While you’re here, though — why won’t the Pinkard translation ever be published? And is the new Science of Logic translation worth the investment?
I had a Kojevean-Straussian political theory professor who insisted on the Baillie translation. He had studied with HS Harris, whose super-book on the Phenomenology is good.
The Cambridge Hegel translation series has had some serious editorial issues behind the scenes; to publish it, Pinkard would have to make revisions he thinks would introduce errors into the text. But he did the translation for Cambridge, so he can’t publish it otherwise. So it’s just hanging out on his webpage now.
I’ve yet to find a passage that was clearer in di Giovanni than in Miller, and it has some unfortunate translation choices; the worst is rendering “Dasein” as “existence” rather than the standard “determinate being”. But it’s worth having for the editorial apparatus. I wouldn’t pay $60 for it, but I’ll pick it up once I find a (relatively) cheap copy somewhere.
Using the Baillie translation is madness.
Peter Dews’ (very very good 3rd-year) module on PhG at Essex left the Preface off the table completely and didn’t seem to suffer for it. Either that or putting it last meant in effect it wasn’t going to be touched by most of us taking the module. The reading was PhG alongside matching parts of Hyppolite and Pinkard’s Sociality of Reason. Not a party, but not a horror show either.
Daniel: that was likely the attraction of using Baillie, plus it’s out of print, so I’m sure there’s some sort of cachet there as in, “All of the translations I read are out of print.”
The only time I’ve seen a writer quoting from the Bailie translation, he also referred to Hegel as “Georg Hegel” throughout. Between those two, I’ve sworn off reading anything from Ashgate Publishing. A publisher that allows *both* of those errors is a publisher I don’t trust with my time. (Not even his mother called him “Georg”; to her he was “Wilhelm”. To his wife he was “Professor Hegel”.)