I'm back.
1. I think a good working title would be: "Operation donate so goddamn much that they cave and begin accepting bitcoin". That may or may not be used publicly depending on the charity.
2. I'm pretty set on doing this for a charity that has some amount of name recognition. Bitcoin users will see the benefit of getting wikipedia to accept bitcoin donations as much more significant than that of getting the Crohn's and Collitis foundation. Go big or go home, ya know?
Are there any fence sitting charities that you know of, who might be into this?