I was going to make this a comment, but then I got carried away..
w3schools has suggestions for using semantic web elements on your site. It suggests using a Javascript library called html5shiv.js to add styling support to IE8 and below so you can find javascript files which emulate specific functionality built into HTML5 like JSON2.js and Webforms2.js.
Finally this article gives a full example of emulating a HTML5 form with many of the new attributes/functionality.
As for building the site, I'd recommend building a HTML4 site first using semantic elements freely (with html5shiv) and testing with IE7. Then as you build parts of the site that require new features, research a Javascript file that will provide older browsers with the same functionality, e.g: when it's time to add your first rounded corner or gradient maybe add CSS3Pie. Always remember as well that your box-model; border-radius and gradients are supported in webkit as well as mozilla's API so many css3 attributes you'll need to add 3 times:
border-radius: 3px;
-moz-border-radius: 3px;
-webkit-border-radius: 3px;
Unfortunately I don't have a good resource for how the webkit/mozilla APIs compare with HTML5 functionality.
The only functionality I've struggled to find is support for CSS3 selectors in older browsers, often you can get away with this, I mean if you're not gonna upgrade your browser IMHO you can live with few double-thickness borders or missing alternate row styling in tables.
Maybe one day there will be a site that you can upload your code to that will tell you things like "chrome 20.xyz doesn't support rounded corners, add -webkit-border-radius
to add support" but until then adding backwards compatibility after the fact will be near-impossible for complex sites.