A difficult part of writing for me is when a single sentence–especially dialogue–contains two tones. It sounds best as a single sentence, but ending with a period, or alternative punctuation, looks wrong. As well as this, using two sentences also looks wrong.
I can’t think of a great example right now, but I know I’ve wanted punctuation that doesn’t exist before. I’ve had moments where it would have been so useful to have a “;!” and a “;?” mark.
It’s a bit harder to do this digitally though since the glyphs aren’t just marks on paper.