All the commands under Append Item for an outline box are interactive. However, you can add button boxes that take a web command entirely through JSL, and they will also work when saved as html. This example adds one link to the 2 subordinate outline boxes. You could add more - I would prepend a v list box to the outline box, and then append button boxes to the v list box.
New Window( "Example",
     ob = Outline Box( "Outline Box",
          V List Box(
               ob2 = Outline Box( "Outline Box 2",
                    H List Box(
                         Text Edit Box( "Top Left" ),
                         Text Edit Box( "Top Right" )
                    )
               ),
               ob3 = Outline Box( "Outline Box 3",
                    H List Box(
                                        Text Edit Box( "Bottom Left" ),
                      Text Edit Box( "Bottom Right" )
                    )
               )
          )
     )
);
// buttons
bb1 = Button Box("JMP Community", Web("https://community.jmp.com"), <<underlinestyle);
bb2 = Button Box("JMP Website", Web("https://www.jmp.com"), <<underlinestyle);
// add them to the outline
ob2 << prepend(bb1);
ob3 << prepend(bb2);
Hope this gets you closer to what you wanted.