Derron,
I had a similar, but slightly different issue that may help you or others.
My client upgraded to Gantry 5.5 and crashed her entire site. The error was:An exception has been thrown during the rendering of a template ("CSS Compilation on file 'gemini.scss' failed on error: $amount: 1 - number('0.9') is not a number.: templates/rt_gemini/scss/gemini/sections/_overlay.scss on line 2, at column 5 Call Stack: #0 import templates/rt_gemini/scss/gemini/sections/_overlay.scss templates/rt_gemini/scss/gemini.scss on line 47 #1 import templates/rt_gemini/scss/gemini.scss (unknown file) on line 1").
The offending line in _overlay.scss was: background: fadeout($overlay-background, 1 - number($overlay-opacity));
Note that it was actually in two locations, Of course, I had to fix both of them.
After reviewing the Helium and Hydrogen themes, I see that RT removed all (as far as I can tell) calculations that include "number(...)" and replaced them with hard-coded values (0.9, as $overlay-opacity = 0.1), so that's what I did as well. Worked like a charm.
So based on what you posted above, I recommend reviewing your scss files (_breakpoints.scss, _header.scss, callisto.scss, and any others that define breakpoints, such as those in the /scss/configuration/ folder). Then determine which ones appear to have conflicting units (rem vs. px) and make them common (i.e. convert px to rem, or rem to px).
Yours is certainly more tricky than my problem, but hopefully this helps.
Cheers!
Stuart