Title Text Wrap doesn't work with handles
Suggest that when any handle is dragged, the text should re-wrap, regardless of when and how entered or how the box was defined.
Suggest that Command-drag any handle to enlarge or shrink the text.
Suggest that with Option-drag any handle to stretch text.
If you use Text-in-a-Box, meaning that you create the Text Box via a click and drag of the mouse and then type into it, then the text does wrap accordingly.
Unfortunately, Text-in-a-Box and Text-on-a-Point (when you just start typing in the Program Monitor) have different features and are not interchangeable.
Text-in-a-Box is a malleable container where text will wrap and Text-on-a-Point contains all the text within the box and scales the whole thing up or down.
So if you want to drag any of the handles on the Text-on-a-Point boxes then the text will enlarge or shrink. If you want to stretch the text, then deselect the Scale lock in the Essential Graphics Panel and change the x or y values independently.
Hope this helps clarify some things,