This may be frowned upon, but I asked my question on the Infragistic forums as well, and a complete answer is available there (along with an example solution demonstrating the problem):
http://www.infragistics.com/community/forums/p/88541/439210.aspx
In short, I was applying my custom editors at the cell level, which made them unavailable when the rows were grouped together. A better approach would be to apply the editor at the column level, which would make the editor available at the time of grouping, and would provide the expected behavior.