Hello Tim,
You can only set the content and the header to be vertical rotated to 90 or 270 degrees by setting TextOrientation property of the Content or Heading.
You cannot display several tooltips together because when the tooltip is displayed there is a check whether the mouse location is over the control which tooltip is attached.
Other similar controls are NPopup and NPopupNotify but both are dialog like and you cannot show more than one simultaneously too.
Best Regards,
Nevron Support Team