I was also having trouble with ffmpeg recognizing Windows paths. I finally just put the font Arial.ttf in the same folder as the input file and it worked.
[drawtext @ 03C66EA0] Key '/Windows/Fonts/Arial.ttf: text' not found.
[drawtext @ 03C66E00] Error parsing options string: 'fontfile=C:/Windows/Fonts/Arial.ttf: text=Test Text:x=100: y=50: fontsize=24: fontcolor=yellow@0.2: box=1: boxcolor=red@0.2'
Error initializing filter 'drawtext' with args 'fontfile=C:/Windows/Fonts/Arial.ttf: text=Test Text:x=100: y=50: fontsize=24: fontcolor=yellow@0.2: box=1: boxcolor=red@0.2'
Error opening filters!