Hey Jim, I am hoping to do the entire JMT next summer, too -- in July. I have a buddy I have agreed to take along. He's never done much of the trail.
You're right about Vermillion and Muir Trail Ranch -- they're a long day, or a day and a half apart. I did the Muir Trail to Kearsarge section about 10 years ago, and it took a full week. It's the longest stretch between supplies. I think you could easily skip VVR.
Pack train resupplies are really expensive--hundreds of dollars.
I don't know about the lottery. Please post more here what you find!
I've always wondered about resupplying at the Tuolumne Meadows-- that would make the haul up from Yosemite Valley easier. Does the store there carry much backpacker food?