Bob, I hope you don't mind I moved your post to its own thread. So many questions, so much we can share with you...
I've added your trip to the calendar. I see Brent N will be on the mountain. Hope the two of you cross paths.

> I've done lots of hiking in Zion and I imagine the extreme dropoffs of Whitney being similar to Angels Landing or Observation Point. So fear of heights/bears is taking a backseat to fear of AMS/pure physical exhaustion.

You won't be as close to dropoffs as Angels Landing. Bears are only an issue at Whitney Portal where day hikers might lose a day pack to a pre-dawn sneaky bear when they set it down and walk away.

With your aggressive schedule, AMS issue can be the biggest problem. Get a prescription for Diamox (Acetazolamide). Dosage is about 1/8 to 1/4 that of the old glaucoma Rx of 500 mg 2x per day. Try one or two doses at home before you come, to make sure you will be ok with it. At the low dose, there shouldn't be any side effects.

...Are you going to be at altitude in Utah in the few days before you come? That will definitely help the acclimatization!

If there is a foot of snow, crampons might help, but this early in the season, I'd skip the ice axe -- snow is just too soft for an ice axe. For that matter, if there is a foot of snow, unless you are a mountain locomotive, Trail Camp might be your turnarond point. If there is no snow, it will be a nice cruise to the summit, with maybe icy footing on the trail higher up.

You might consider overnighting at Outpost Camp -- lower elevation, more protected, so not as bone-chilling cold, AMS much less of a problem. The summit is quite reachable from there.

> 4. How many people do you think will be up on the mountain? It would be cool to see a constant stream of headlamps milling about at all hours of the night.

From last year's Unused Permits page, there were only 20 or so overnight permits given out mid-week in October. And in my experience, you may only see about half that number of actual hikers (not sure why that is). Although the reservations are all used up, the majority will be no-shows. So you're likely going to have one of those highly sought-after "outstanding opportunities for solitude" wink

...I'm sure others will help out with more of your questions.