It appears the Tool Tip does not hide automatically (at all) when it is shown overlaid on the right click menu. It keeps hanging there until I click somewhere (in the menu, on the map etc.) to make the right click menu disappear first.
Menu items that are obscured by the tool tip are not marked when I hover over them (so they appear to be unaccessible) but do work if I click on them. So perhaps this is more about aesthetics than functionality.
But I guess in these cases it is still desirable to have the tool tip hide according to Tool Tip Hide Delay value rather than stay there.
And perhaps display the right click menu always above the tool tip?
You may notice this in hexes where the two can overlap if you right-click fast enough and/or increase the Tool Tip Show value (Player Options) to 300 or 500 for example.



