I think what we're really thinking about doing is preserving IE8 for the existing gwt widget stuff, but any features (APIs) we add going forward are going to leverage modern browser stuff, and we are not going to design (poorly performing, hacky) fallback/polyfill workarounds.
For GWT 3.0, we are looking at making a new, parallel way of writing Web UIs that is based on the emerging Web Components standard, and we will lean heavily on modern browser layout engines, e.g. flexible box model. We're not going to break your existing apps, but we're not going to make these new models work on old browsers. For example, to make data-binding working efficiently in Web Components, you need mutation observers, Node.bind, Object.observe(), etc.
We are not going to require Java7 or Java8 to run servlet code or even invoke the compiler, but we will support compiling Java8 code to JS, and we'll have super-sourced versions of java.util.function/java.util.stream.
Basically, the future is easier interop with the browser APIs, external libraries, and web components, and less reliance on heavy weight widgets that run lots of JS and shield the browser. This is a vision more in tune with the fact that mobile is increasingly becoming a bigger and bigger chunk of the web, and the original GWT metaphor of a Desktop-like AWT/Swing-like UI library with layout done by executing code is less efficient on mobile and is suboptimal for fast browser jank-free execution. We don't want to break existing applications, and we don't want to hamper designs for the future by requiring them to work on ancient browsers.