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Three summers ago I undertook a similarly insane venture: The AIDS LifeCycle (see aidslifecycle.org), a 7-day, 585-mile ride from San Francisco to Los Angeles. It was a life-altering event, and here are some things I learned that are pertinent to Andrew's questions:
First, California is really big. And most of it isn't Toll Brothers tract housing (at least not the routes we took, which focused on Salinas Valley agriculture, Santa Maria hills and Pismo Beach coastland). It's spectacularly beautiful. Yes, land planners are doing dumb things, but it's eclipsed by our natural environment.
Second, you'll have valuable insights irrespective of whether you can research them on the Web or not. You've been doing HTWW long enough that you'll see unseen connections in areas in which you're already an expert.
Third, don't worry about the physical problems. If you can ride a century already, you're fit enough. Everyone's rear-end hurts like hell by Day Four, even if you're a skinny little dude on a $5000 Seven. I was one of the fattest riders during my ride and I still pedaled every inch.
