May be it is time to rewrite the tooltip and popover and outsource the complexity of position calculation to a specialized pluglin like PosititionCalculator . OK, that is from myself but it does what you need.

Then the bootstrap tooltip and popover only need to apply the calculated position, add the correct class for orientation (to get the arrow to the right side) and manage events.

Here is an simple example: http://jsbin.com/sifec/9/edit?html,js,output

You would get for free the auto position with flip and stick depending on a viewport / boundary with 9 possible placements instead of the 4 you now supports.

That could solve issues like this:
#14322, #14323, #14197, #13934, #13897 ...