I use a Dragonfly Red out of my iPad into my HIFIMAN HE400S ‘phones, and I find it to be very neutral and open with good tonality end excellent imaging, air, and dimensional out-of-the-head soundstaging. I’ve read some reviews of the Nano, and several mentioned it’s slightly on the laid-back side and can make bad recordings more listenable. The Dragonfly won’t do this as much, so from a sound perspective that might make your choice an obvious one depending on what you’re looking for.
As far as other differentiators, the Dragonfly is much, much more convenient and portable, but the Ifi counters with more power and more features. So depending on your use case this could also skew you one way or the other. Hope this helps, and best of luck.