Between the Dragonfly Cobalt and the Dragonfly Red, I thought the two definitely had a family resemblance in their sound. The Cobalt MIGHT have been a litter clearer, but not too different from the Red especially after adding a Jitterbug. I actually decided to get a Red over a Cobalt as it sounds more punchy which I think works well as I'm often listening on the go in different locations.
The real step up from a Dragonfly that I've heard is a Chord Mojo that provides greater 3 dimensionality and presence. You can get a used Dragonfly Red on eBay for about $140 to $150 shipped.