Comments:

Question A1: I think the determinant of the primary purpose of the commercial email should be whether or not is was solicited. Many newsletters include advertisements, some are made up entirely of ads. Small business owners will also send out straight ads for a new product or feature. The main focus would be an ad, but if it is requested, it should not be labeled as commercial email. Question B1: I do not see newsletters and web site updates included in transactional mail. Most small online business would not be able to operate without sending these kinds of messages. Question B3: If someone opts in to receive transactional mail, the content of that message is irrelavant. It is expected that subscribers who object to the amount of ads they receive via transactional mail will unsubscribe. Question E.1-2: If I understand this question correctly, the scenario would go like this: Mary unsubscribes from a program and then receives a message advertising said program from another source who has not received an unsubscribe request. As long as the second source provides a functional opt out process, no violation has occured. I don't think it matters how many ads were included in the message from the second source, the second source is responsible for the email. Today, many small business owners are adopting a double opt-in process with their mailing lists. If we have proof that someone agreed to receive emails from us, we should be able to send them a variety of messages without risk, until they unsubscribe.