I like this journey thread, it is meticulous.
I would suggest to publish books in bundles or be ready to go back in and edit a work.
One of the best tips I discovered the hard way was to have EVERY book end on a Cliff Hanger, and to give a link to the next work. Even if the work goes no where, an email address to contact you to add to mail chimp for those who like your work is free marketing.
I am sure you did homework about marketing, and Eben is a brilliant man. First hand, I know he has a firm grasp on making money off of any idea. Kindle is fairly straight forward.
Two approaches really work. One is the spam book approach. The other is getting investment from clients and getting them to continue to buy your books. You are buying your work so keep in mind that your writers need to be seeding in events which can be expounded upon later. Loose threads are HUGE for income later on if one of your works become a hit. Evidence of this is in every 'huge' series. Fans have questions, and authors make money to answer them.
Due to the fact you mentioned Eben and guys good with girls, I would STRONGLY suggest you look at the PUA community for advertising ideas. Often, they do not view as other as competition, everyone can make money. They often team up and share email lists. If you can get someone in the same niche who is doing well to promote your book on his network you make free money, and doing it in return builds you list as well. People will always buy books, and crafty authors love the notion of free advertising and people with no experience will jump at the prospect. With very little work on your part you can expand rapidly with promoting your books.