Hey Alan, my initial thoughts, if you've given these consideration forgive me if I'm repeating the obvious.

I see two sides to it - there's the technical side of understanding how specific blacklists and filters work. You can find out how they document procedures to get your list cleaned. E.g. are you going to be sending to Yahoo addresses? This post might help getting around blacklists there, and I'm sure each one has lots of docs on this issue.

The other side is user education/interface, where you need to avoid getting your mails flagged in the first place. The normal stuff like having your company name in the Subject:, having a big "You are receiving this because" block up the top and a single simple one-click unsubscribe option that works.

Pull out all the tricks to avoid getting reported and have a strategy in place for the major blacklists to get back online if you are.