Sounds super frustrating. When I have run into this, it is almost always:
* Text wrap
* Keep Options

If you use the Selection tool to drag the text frame out on to the pasteboard, does it change anything?

No, animations don’t work on buttons, and they don’t work in interactive pdf. (Well, they kind of can, but they’re really for Flash right now.)

I’m not a scripter, so I’ll leave that question for someone else. But you know that InDesign CS6 and CC have Auto-Fit for text frames now, right? In the Text Frame Options dialog box.

Where did you buy it from? I’m guessing that it is an applescript of some sort.

There are other tools out there, such as:
https://zevrix.com/linkoptimizer.php

Not sure if this helps, but: https://creativepro.com/book-panel-shows-wrong-page-number-fixed.php

Interesting that the script no longer works. Do you get the sense that Photoshop is breaking it, or InDesign?

I don’t use any scripts like that. I don’t worry about getting it exactly 100%, but I do agree that it still important to get close. I try to be within 10 or 20% or so of the size on page. The main reason is that when InDesign downsamples the image (at print or pdf export time) high res images can get blurry, and usually require a bit of sharpening.

Hm… no, I think InDesign works the way you want it to. If you give a paragraph .25″ space after, and then the next paragraph .25″ space before, then you have .5″ between them. No?