I've had that question a lot... so I thought I would answer in this blog.
I have made a commitment to get David through his Senior Year of High School at this point. That would a total of 5 books of about 750 pages each. Each chapter is 20 to 30 pages. It takes me a week to write a chapter... if real life doesn't hit. So a 30 chapter book is 30 weeks of just writing. Then the editors fix all the junk I wrote and there are rewrites. One book can take 45 weeks.
So buckle up. I would guess that Book 3 will be ready in 2015... Book 4 2016 or 17 depending on projects and Book 5 2018.
I have thought about college and beyond. But no commitment at this point.
After Book 3 I think I will step away from David for a while and write some normal sized books. I have about four of them fleshed out in my head.
The problem I am having with Stupid Boy is the timeline is current. Real events effect which schools he would be looking at for recruiting. Will they be paying college athletes? If Northwestern pays and Alabama doesn't does Northwestern suddenly become a power house. Does a medical study show that football really does mess up your head and David should play baseball.
When I started I was convinced he would go to Florida for college... Kentucky was just a fun lark... If he had to pick between the two today it would be Kentucky. They just landed a top 15 recruiting class and are 5 - 1. Ironically their only loss is to Florida in a triple overtime thriller.
At the beginning of the season I loved Texas A & M and Alabama... Ohio State was in mix. How about USC losing on a last second hail marry. AHHHH! Could it be that Notre Dame finally has their act back together.
It is so much easier to write something that is not current. If I had to do it over again I would have started in 2005.
The short answer is a total of 5 books ending in David's senior year.