Paul,
You need to ask yourself to whom does the array belong? It doesn't belong to the Add button becasue the Send button needs it and it doesn't belong to the Send button becasue the Add button has to populate it so then who doe sit belong to? It should belong to the thing that owns the two buttons, the form.
So you go to the fomr designer and add a property to the form named aFiles(1). Then in the Add button you dimension and populate Thisform.aFiles() and in the Send button you can read Thisform.aFiles().
You see it is all about who owns it.