I have seen the future of typography and its name is Liza Pro.
I’m sure there are other fonts that do this out there, but Liza has a character database of 4,000 letters – it will, in the right design software, change which version of a letter it uses based entirely on context.
“Liza Display Pro rocks the script lettering to the max. The build-in Out-of-ink feature, LetterSwapper and Protoshaper makes this font a realtime-digital-calligrapher. She’ll swash up your text drastically, giving long strokes, loops and swashes to letters if their context allows”
Clever. But expensive.