On older versions when you added a Simple Text Overlay on video track 2, there was a Fading checkbox on the text editor that accomplished what I desire (i.e., any text overlays fade in and out over the image/video on track 1 instead of appearing abruptly).
That seems to have been removed (in this case using 17.16) and so far the best I have found was adding a Fade Out transition to the overlay clip and then adding another empty text overlay before it with a Cross Fade transition.
There has to be something I am missing!