This is a prime example for what a service layer is used for.
I think a layered approach is best here. I would start at the bottom with a Data Access Layer (DAL) using the Entity Framework or NHibernate. Then you can put a business logic layer on top of that and then put a service layer on top of that.
All the while both your windows and web apps can use each layer as it comes on line. I'm reading Microsoft . NET: Architecting Applications for the Enterprise by Dino Esposito right now and it is very helpful with these types of problems.
I cant really gove you an answer,but what I can give you is a way to a solution, that is you have to find the anglde that you relate to or peaks your interest. A good paper is one that people get drawn into because it reaches them ln some way.As for me WW11 to me, I think of the holocaust and the effect it had on the survivors, their families and those who stood by and did nothing until it was too late.