I remember messing with 5 level grayscale in xLIB before, but Nitacku's ditherer was not out yet and making sprites was a major PITA, since most softwares only allowed 4 level conversion. It didn't flicker incredibly bad, but it was 15 MHz only, due to the nature of TI-BASIC.
I never saw any 5 level grayscale game on calcs, though. The issue with 4 level grayscale and higher is that on the regular 83+ the contrast is so weird that we barely see one of the shades of gray.