It might be insane but, why Guido should be concern with every framework built atop Python? As far as I see it, it is not really his business after all.
But, on the other hand, I totally agree with Jonathan when he says that the Python community should only focus on some solutions though I think we should act on two levels.
I've found all that burden around Rail really sane for the Python community which sometimes is really quick to think Python is the best so we don't need to keep on going on. Python community is a bit self-centric sometimes where Ruby community is not ('till now).
That's why I also don't think Guido should have anything to decide in terms of web frameworks. We can't rely only on one unique individual.
Just y 2 cents...
Why should Guido concern about web framework? Let's scroll back to the top to check on Ian's key premise.
"Resolving Python's problems with web programming is the most important thing we can do to market Python."
So Guido does not directly invoked in any web development himself. But I bet he would concern about the market of Python and he would be a cheif evangelist himself. And here our believe is positioning Python as a premier web development tool is the top most important thing you can do to market Python.
I don't expect Guido to have any role in designing of picking the best framework. The best thing he can do is to be a catalyst to help the community to arrive to a better solution.
By the way I like your idea of having several layers of framework (like JSP and Struts). If the higher layer is build on top of lower layer that would be even better.