@Hitch
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FWIW, we're not using any second CSS sheet at all. Don't know if that helps.
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Well, it's helpful to a degree, but in effect not really... it narrows the solution down to, what, 10, 1000, 1000, an undetermined amount of possibilities? I assume your solution is an company secret, so it's alright.
In any case, I did some further experiments with my @import method. Here's what I got:
EXPERIMENT #0 - to re-check if the problem persists
Setup: 1 main linked stylesheet containing the actual CSS rules; No @import rules used anywhere; normal font-family definitions used to trigger fonts.
Result: Fail.
What happened: KDP stripped the font-family rules (the whole line no matter of its content, not just the font name that's being referred to) from the main linked stylesheet. As before, the font files themselves, as well as @font-face declarations, remained intact, but useless without the font-family rules.
EXPERIMENT #1
Setup: 1 main linked stylesheet containing the actual CSS rules + 1 dummy & unlinked stylesheet (blank, acting as a decoy); No @import rules used anywhere.
Result: Fail.
What happened: KDP stripped the font-family rules from the main linked stylesheet. Obviously, simply having a dummy style doesn't prevent KDP from making away with the fonts from the main style.
EXPERIMENT #2
Setup: 1 main linked stylesheet + 1 mirror copy unlinked stylesheet containing all the styles from the main; No @import rules used anywhere.
Result: Fail.
What happened: KDP stripped the font-family rules from both stylesheets.
EXPERIMENT #3
Setup: 1 main linked stylesheet containing
only the @import rule + 1 unlinked stylesheet containing all the actual CSS; unlinked CSS imported into the linked one via @import.
Result: Success. 
What happened: No fonts stripped from the unlinked CSS. Tested on several books. Fonts show up on both the Offline and Online Previewer, on Kindle for PC, as well as in the actual file when inspected. I confirmed the CSS remains intact.
Now, why this works I've no idea. But it does, and it's easy to implement. Kindle devices support the @import rule, so I'm gonna stick with that.