I'm not sure what you are expecting. PDF is a final output format, not really intended for editing or text reflow, so it's not unusual for text to be broken into fragments. Since we can't see your page I can only presume there is some sort of wrapping around the image goin on to cause this.
Is it affecting the way the screen reader reads the text?
The part on the left is page 1, there is a text box with an anchored image with text wrap and a directional feather effect, it is tagged in the structure window and exported with tags. that works fine, the text does not get carriage returns at the end of every line.
Image on the right has 2 anchored images in the text with same effect as above and same deal with tags. that turns out wrong, the end of the text lines have an carriage return added to it.
If I then remove the effect, you get the correct text flow again.
So the anchored images it self is ok no matter where in the text block they are placed, but when you add an effect something goes wrong.
And yes it affects screen readers allot, it will read the text as there is a carriage return on every line, and it sounds wrong when there is a pause that shouldn't be there.
Atm I can only remove the effect to make it work, if you have pages with multiple images.
I don't have an answer for you. It sounds like a bug if it's OK with one image, but not two. Perhaps Dov Isaacs will have something to add.