Let me first make this clear: each time you fix something for a certain browser, you are not applying progressive enhancement. Progressive enhancement is all about building for the less capable first and enhance the experience for those using the latest modern browsers. So, any type of fixes are useless. If you use fixes, you might be applying graceful degradation or, more likely, you may just be hacking around in order to workaround the differences across the browsers and to make everything look and feel the same.
One of the great features of html5 is the new semantic tags. Like section, article, aside, footer, etc. Let's see how we can build a new layout using them. First of all, we have to make them block-level elements with css since they will behave as inline in each browser that do not understand them. So we fix the fact that these browsers do not support html5 semantic tags. Oops, I used the word fix, that's an indication we're not applying progressive enhancement. Ok, that's a tiny little fix so we can ignore it. Now, another obstacle is that Internet Explorer cannot apply a style to elements it doesn't know. So we're using the html5 shiv to create the elements in the DOM Tree and to fix this bug in IE. Oops, another fix. I'm not going to continue, I believe you get my point.
Ok, but what about the degradation of our future highly semantic markup? When you apply these fixes, another issue to worry about is what happens on browsers that do not support css. All these block-level elements becomes inline and the page looks messy (remember the idea of the CSS Naked Day?) The same way as if you use only spans to build the layout. Or what happens to IE with JavaScript turned off. It still cannot see the styles related to the new elements. So, our degradation is obviously not graceful, it is, to be honest, painful to watch.
The fact is, html, no matter which version, is not related to the user experience in any way on a given web page. It describes the data on the web, it marks it up. That's it. No visualization, no behavior. So, how can we build html5 layouts using progressive enhancement? Which is the basic technology we can use before it to assure wide support? Yup, there isn't any. Of course, we can build our layouts in the old way, but then we are not really using html5, only these features that work across the different browsers, like the short doctype, short charset, etc. That's a kind of compromise, it's neither progressive enhancement nor graceful degradation.
A great example of html5 and graceful degradation is Video for Everybody! on camendesign.com. It uses html5 video features, then it fails to QuickTime if your browser is not aware of html5, then it fails to flash, then it fails to image. But can't we reverse the process? Can't we build for the one that is unable to see video by any mean and then add flash, QuickTime and in the end - html5? I think it cannot be done right now, but it's still a not explored field. I might be wrong...