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Having done Whitney as an overnight backpack in 2001, with two nights at 8,000' in Mammoth Lakes and one dayhike to 11,000' worth of acclimation first, I'd be leery of flying back to CA and hitting the main Whitney trail the next day. Remember, you'll have been (literally) at sea level in HI and will have had a fairly long (5 hours) flight at cabin altitude (8,000' or so) before returning to sea level at LAX.I'm planning my trip for September 21-29. I've already applied to the California lottery for the main Whitney Trail with 2 choices. The first is 9/26-28; the second is 9/23-25. IF (big if) I get my first choice, that will leave me with all day on the 22nd and 23rd to play in Hawaii with one of those days for Mauna Kea. The 24th would be the day up in the air. Do I go to CA on that day and give myself plenty of time to get to Lone Pine for a mid-morning start on the 26th OR to I leave on the 25th and have a semi-hectic travel day getting to the Whitney trailhead in time?
I like your coin flipping method and really feel like 3 days is a boatload of time for Whitney. I'm fairly confident I could dayhike it but 6K elevation gain is a lot at altitude for a lowlander and I don't want to chance it. Anyway, I'm looking forward to it intensely.