Hi Chip,

Nice! Are you using version 12? On 11.3.0 for Mac OS X x86 (64-bit) (March 7, 2018) some letters do not discretize

Cases[$letters, _BoundaryDiscretizeGraphics]

{BoundaryDiscretizeGraphics[Text[ Style["h", Italic, FontFamily -> "Times"]], _Text], BoundaryDiscretizeGraphics[Text[ Style["i", Italic, FontFamily -> "Times"]], _Text],
BoundaryDiscretizeGraphics[Text[ Style["j", Italic, FontFamily -> "Times"]], _Text], BoundaryDiscretizeGraphics[Text[ Style["k", Italic, FontFamily -> "Times"]], _Text],
BoundaryDiscretizeGraphics[Text[ Style["y", Italic, FontFamily -> "Times"]], _Text]}