i can help you experiment with the popup bar part
do you have a copy of the classic OB theme, the one that looks like win98 / win2k ? my OB theme is based on this, and it is a good simple example showing how to do this.
in the theme editor, my start menu (win2k style) has an item called "Settings", which is of behaviour class "Popup Menu Item".
because of this, i can set (on the behaviour tab) which bar (or even bars) to popup when i activate (mouse click, keyboard enter) this item.
nice and simple, when you know to do this. of course, if you dont, it is totally confusing

i remember being confused by this myself

if this doesn't make sense, we can pick a simple theme, and experiment in parallel with it
with regard to the ultimate OB theme, does it contain:
* dual taskbars
* SDTaskManager plugin showing 3 different graphs
* keyboard access to my desktop shortcuts
if not, then how can it be the ultimate theme?
there are even two flavours of it, one for work, and one for home