I think it really depends on the type of site you are building, as well as the type of intended end users. If you create a site for a group, they usually use a lot of flash / silverlight to make the interaction “cool” and more fluid. This will be an example of when you need to struggle to use HTML5 and use the canvas to perform some of the same effects. It’s obvious that IE6 will not work, but as more and more large companies refuse to support IE6 (Google is enabled for gmail), over time there are less and less problems.
If you need to develop a site where people will continue to make heavy use of IE6, you may need to avoid using the latest technology. The pain that you could have gone through to get you working might not be worth it in the end, especially if the deadlines are tight, and if you are not an expert.
Then there are cases in the middle, and here I think you need to think long and long if you want to support IE6 support. I know a group of people who have refused support, and it has become much easier to balance between CSS3 and HTML5 with other browsers. It is still not perfect, but it is much easier to work with it.
amurra
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