I understand you are frustrated.
The technique to get your menus to show properly is to go to the menu writer wizard and update the column width so that your text fits. Change the label to "tournaments" instead of "2008 -2009 Tournament Schedule". Any other solution would require at least re-opening and running the wizard if not making hand edits which you want to avoid.
Since our menus use css and lists, some are positioned relative to the menu before allowing them to appear on the right. When you set the width of the menu, it automatically positions the submenu according to the width.
I don't think I can solve your frustration. The menu writer does what it does and has restrictions inherited from its architecture, in this case cross browser compliant lists with css. Some things are tricky to do and some things just aren't possible.