Check out the MSDN TV episode "Drag Once Databinding for Client Apps". A couple of years ago, I spent some time attempting to get object properties to appear in the data binding selection lists of Visual Studio. It was ultimately futile as it seems the VS design at the time was purely oriented to the Ado.Net world. There wasn't as much information on the how the databinding and component model worked (including such classes/interfaces as IEditableObject, IBindingList, ITypedList and TypeDescriptor) as there is now. I still don't think the documentation that Microsoft supplies really covers this area in an organized coherent manner. Sure there's lots of bits and pieces articles but nothing that describes the System.ComponentModel and databinding as a coherent whole. On the plus side, there are third party articles like this one that are gold when you come across them.
With respect to the object data binding I remember hassling Chris Sells via his shortlived Ask the Wonk service (experiment? product? forum?) about how to make VS2002/2003 more object structure aware within the IDE. He wasn't a Microsoft employee at the time so there probably wasn't a hope of finding out if this was possible, but it was worth a try since I was hitting brick walls.
Back to the present, the VS2005 ObjectDataSource functionality looks very promising as a means of achieving what was attempted a couple of years ago. I've installed VS2005 Beta 1 but can't justify the time to experiment with it in detail. I just wish Microsoft would stop demoing ADO.NET oriented data binding and show what the ObjectDataSource functionality looks/works like in MSDN TV or a Webcast? Roll on the MSDN TV session showing object data binding in VS2005! Actually for that matter, roll on the VS2005 release. There's so much goodness in it that it's tough waiting.