Would you be able to get away with hiding/showing checkbox columns?  In such a case, you could probably use a Binding object on the Visibility property of the columns in question, along with a Boolean-to-Visibility converter is they are shown/hidden based on a Boolean value in your data.

If this approach would not work, please explain in more detail what you need to accomplish, including what the presence of the dynamic checkbox columns would depend on.

Thanks,