Text elements have a property called Keep Readable. This prevents the text from being displayed upside down and reorients rotated text elements so they are "readable" from left to right and bottom to top. As soon as text transitions past 90 degrees and then between 180 to 270 you'll find the text flips to ensure that it is easier to read. All of this is true for text in a project view.
In a family the text elements share this parameter but it doesn't matter if you check it or not because the family governs whether text remains easy to read. This setting (Keep text readable) governs all text, even nested label families, in the family setting.