In .Net 2.0 it's possible to define custom properties for a typed Dataset and retain them when the code is regenerated, thanks to the wonders of partial classes.  I was writing a UI prototype recently for a Windows application, and used typed Datasets and TableAdapters to speed up development. 
It's always been possible to define an expression for a calculated column in a DataTable, using a syntax that I think is supposed to remind us of SQL.  But you're limited in what you can put in there, restricted to a few defined functions.  To pick one example, there is, as far as I can tell, no way to specify that the current date be used as one of the expression's operands. 
This led me to writing a custom property for my typed DataRow, one that used some business rules about effective dates and anniversary dates to calculate a duration.  In Object Explorer, this property looked like all the others.  Could I use it in Windows databinding?
The answer appears to be "No", although I haven't found anything written about it one way or the other.   But it won't appear in the Property window's field picker, and specifying it leads to an runtime error.  I don't know the reason for sure, but I suspect it's because the object you're connecting your controls to when you bind to a DataTable is really a DataView.  A custom property on the typed DataRow wouldn't be accessible through a DataRowView. 
And this is a pity.  When you're writing a little three-day minimum-investment project like my prototype, you want an easy, clean solution, one where you do the hard stuff once if at all and don't lock yourself into any particular architecture.  A typed DataRow that could expose bindable custom properties would be a good stand-in for the custom business objects that it's too early in the project to create.