Eduard Metzger: That's quite possible! I'm coming from a CSS background, but wouldn't it make more sense to sit a fixed width for both bullets and dashes so indentation always matches? That way you could mix dashes and numbers and you'd know everything is always going to line up on every line. (I don't think this would be easy; it's just my inclination.)
Nathan Snelgrove: Yes, that's done when you enable rendering. Then the task icon is always the same and fixed. Not sure if I can fix the width for every font though. To be honest, it was just a guess, I'm not sure if this is even the issue.
Eduard Metzger: And to be honest, this is a pretty small problem, so I wouldn't expect a fix for it. Just a note on it. Everything otherwise looks great and lines up with Render Markdown enabled, but this is just the one bugaboo with basic Markdown.
Might be that the dash has a different width with this font?