I think some of the confusion might be coming from you attempting to draw conclusions about the behavior of digital audio in general by observing the behavior of an ancient version of cool edit. None of us can replicate your results, so that might point to cool edit being silly instead of giving you much usable information about the behavior of digital audio.
Well it isn't hard to figure out but if you want alternate methodology try this:
1. Generate a sine wave on your computer. I used 440 HZ, probably isn't too critical.
2. Print it at -24 dBfs
3. Save it as a 16 bit file.
4. Attenuate it by 60 dB
5. Save the attenuated version as a different file.
6. Close all files and your software. You've flushed all the caches, you're not in 32 bit float or something, you've rendered the file to the destination format. The damage is done.
7. Open the attenuated file and amplify it by 60 dB.
8. Play the file. Compare it to the one you didn't attenuate.
If it's a sine wave bathed in static you have dithering enabled. If it's a square wave, there's no dithering. If you want to try it without dithering to find the point where it starts to truncate (probably around -60 dB or so) have fun.
Try it. Or not. I don't care!
I didn't just invent this. If you want to learn about it yourself, try a few basic links - it's not top secret information although a lot of the more detailed resources are full of scary looking math.
Audio bit depth - Wikipedia, the free encyclopedia
Quantization (sound processing) - Wikipedia, the free encyclopedia
Analog-to-digital converter - Wikipedia, the free encyclopedia
The last link goes into a bit of detail about other converter issues but covers quantization pretty well.