I've been playing with color contrast for a bit, but I'm not sure if it's just my eyes/monitor that is biased:

Which one of these is easiest/hardest to read for you? (most/least contrast)

According to APCA (https://git.apcacontrast.com) all five have the same Lc of 30.

For me 1 & 2 (light on dark) are much easier to read than 4 & 5 (dark on light)

APCA

This is the APCA project repo on GitHub.Documentation linked below.

APCA
@Typeface same for me. I think that maybe it has to do with thin dark glyphs being “engulfed” by the light of the surrounding pixels, quite the opposite to print glyphs, where a white text gets engulfed by the surrounding dark ink.
You could make a test with very bold fonts just to check if the weight of the font is the issue
@fdrc_ff good point, that could skew this particular test. I'll have to check if the APCA calculation embeds this. If it doesn't then dark-on-light should use a higher Lc value than light-on-dark, to get the same perceived contrast (for smaller fonts).