Hi Agent - AFAIAC, the AI option that you are using, ie,
"display and print as rich blacks" is the devil's own work, LOL, and should rarely, if ever, be used. IMHO, this setting causes vast amounts of confusion, especially when coupled with possible monitor calibration problems.
Instead, try this little experiment:
a) First, if you have a hardware calibrator, re-calibrate your system before you do anything else.
b) Read
My Old Post In This Thread, open AI, and as stated in that post, set your preferences to
"Display All Blacks Accurately" both for on-screen display, as well as when printing and exporting. Then open a new test AI document using those preferences, re-do (from scratch), your filled-circle-inside-a-rectangle test, and see if most of the problems that you've been having go away.
The reason I said,
"most of your problems", not
"all of your problems" is because of your statement,
"...They read as different colors in the color picker, but on my monitor they look almost indistinguishable..." yet I observe them to be clearly different both to my eye, as well as when I use an eyedropper in Firefox, or if I download your image and use PS's eyedropper. AFAIK, the only way you can be seeing one thing, and I am seeing something different is if one of us has a monitor calibration problem. Prompted by this thread, I just re-calibrated my monitor. There was almost no change from my last calibration, so I'm pretty sure that what I am seeing is correct, whereas I suspect your system is slightly clipping your blacks when displayed, and that, coupled with the AI preferences you had been using is what caused your problems.
Obviously, there are other things that could be wrong, but why don't we see if we can land a hole-in-one solution, LOL.
Cheers,
Tom M