I have an issue similar to the following post:
Silverlight DataGridTextColumn Binding Visibility
I need to have a Column within a Silverlight DataGrid be vis
Note that the problem isn't just as simple as 'Visibility' not being a dependency property. In a DataGrid the columns aren't part of the visual 'tree' so you can't use AncestorType even in WPF (or Silverlight 5).
Here's a couple WPF related links (please comment if any of these work for Silverlight - sorry I don't have time to test now)
Has a really nice explanation of the problem and failures of certain solutions (and a clever solution): http://tomlev2.wordpress.com/2011/03/21/wpf-how-to-bind-to-data-when-the-datacontext-is-not-inherited/
And a couple StackOverflow questions:
WPF Hide DataGridColumn via a binding
Binding Visible property of a DataGridColumn in WPF DataGrid