wazzu, welcome to the board. Lots of good folks here who will assist you any way they can.
From my perspective, you've tackled the biggest potential problem based on your last attempt - elevation. That headache that turned you around last time was almost certainly altitude-induced, and your plan of sleeping multiple nights at 10K' should solve any potential AMS issues. That combined with some relatively easy dayhikes to 11K' or higher should get you to 14,505' just fine.
The one potential problem I see is your start time - if I'm reading your post correctly, you're planning on starting the trail well before midnight in order to be at the Whitney Zone sign
by midnight? There was some debate on this last year on the WPS, and I believe the final word from those that know best is that your permit does not allow you to begin on the trailhead at the Portal till midnight. I know - that first 2.5 miles is not in the Whitney Zone proper and would not appear to be excluded, but apparently it is in Inyo's definition as the permit is technically for the Whitney Main Trail and not just the Whitney Zone. My take on it was that a ranger could easily turn an early entry around and back to the trailhead to start over. Likely? Probably not, but it would be a cryin' shame to have it actually happen. I wasn't able to find the thread this was discussed in, but I'm sure you'll get some clearer information soon from Steve or other experts on the board.
Not sure what you're going to eat at the Portal the night before your hike if you're holding off the burger and fries till post-summit, but I would strongly suggest you carb up for that 22 miles coming in just a few hours. The most common estimate is that a Whitney dayhike burns 6000 calories, so fuel is a big deal. A big plate of pasta has been my choice each time - before my summit day two weeks ago dinner was stroganoff with a spaghetti chaser. Also, get as much sleep as possible in the the 48 hours prior to your start since you plan to hit the trail extra-early.
You've made it to Trail Crest before, so you know the demands on your legs - both up and down. If your training has been geared to handle that 6000'-plus elevation gain, and you've got the plan for acclimation, then weather may be your only real enemy. I think the first snow on Whitney last season was early October, but that was last year. It's the Sierra - it could blizzard in September . . .
Best of luck, and be sure to post a TR!
