This thread actually made me join SP. I've been lurking for a couple weeks and now actually have something to contribute.
I hiked the HST during the last week of this past July. My buddy and I did it 6 days ending at Whitney Portal. Our itinerary was as follows:
Day 1: Crescent Meadow to Bearpaw Meadow
Day 2: Bearpaw Meadow to Big Arroyo Junction
Day 3: Big Arroyo Junction to Kern Hot Springs
Day 4: Kern Hot Springs to JMT/HST Junction at Wallace Creek
Day 5: JMT/HST Junction to Guitar Lake
Day 6: Guitar Lake to Whitney Portal
We actually didn't camp exactly at Guitar Lake. There is a tarn just above Guitar Lake with only spots for few tents. I suggest staying there if you don't arrive to late and there is still room. Its less crowded and its gives you a little extra head start in the morning. Furthermore, I don't think an acclimatization day is really needed as said before. With camping at Crabtree and Guitar you'll have 2 days over 10,000 which should be OK unless you really have trouble adjusting.
We did the whole trip without bear canisters by using the bear boxes at each of the campsites. However, Guitar lake is the only spot without a bear box. I was more worried about the marmots than any bears. We just put our noisy cooksets on top of our food to act as an alarm. Luckly we got through the night without incident.
You said you were worried about securing a permit for the Whitney Zone. I'd recommend just hiking out from the summit. Its a long day but you'll be wanting to get away from the hordes of people at trail camp and get those burgers and beers at the Portal. Just get an early start (we got up to the summit for the sunrise) and then had all day to get down.
a detailed trail breakdown (not done by me). I actually printed this and took it with us. It was extremely helpful.
If you got anymore questions, just ask and I'll try to answer. Good luck!