Posting a Chapter From a Book: Fair Use?

Dear Rich: We are planning a discussion of a book chapter written by a professor who will also be attending our meetup. I own a copy of the book, and would like to scan and send the chapter so everyone can read it in advance and be prepared. However, I'm not sure if that is fair use. Would posting the chapter, with a link to Amazon to buy the whole book, on the meetup webpage be a problem? (We have about 400 names on our list.) Would sending the material to only those who sign up on the meetup page (usually only 10-20 people) avoid the issue? Can the author scan and send the material himself (or give permission) without copyright violation?  It's unlikely that posting a complete chapter of a book online would constitute fair use. Check out the fair use cases permitting use of text and you will see that using more than a few hundred words is usually difficult to justify as a fair use.
But the professor is on your side. Because the professor/author favors your use, you probably won't have problems. As we discussed in a recent post, the author may have the right to permit copying. But even if the author doesn't possess that right, the publisher might not want to get into a dustup, particularly if you limit the reproduction to the 10-20 people who will actually attend the meeting ... er, meetup.