OWIN was the first step towards elegant design for the whole asp.net stack. By separating the hosting concerns from the framework, Microsoft was able to build modular services and add it to the stack such as Web API, SignalR and now the whole asp.net core.
Katana was the first implementation for OWIN on IIS, you won’t feel much change as it is still running using the System.Web assembly but at least it enables you to run your middlware under IIS.
To understand more about the motivation, the moving parts and samples of OWIN, you can watch the following video in Arabic.