I want to add a feature to my Mac app inspired by the Help mode in iPhoto for iPad, pictured below. I would love to do this using built-in APIs, so I don’t have to build my own tool-tip-like view. Is there any way for me to either show multiple tool tips at the same time, or to achieve something similar using NSHelpManager?

If you are targeting 10.7 or later you could do this fairly easily using
NSPopover. You would have to create quite a few popover windows but it isn’t difficult to do.