I am actually partly quoting an Audioquest technician I spoke to about the Cobalt. He said Red is really the best for most people with high end head phones. Black for the remaining 95% if they even need a DAC.
The key, as you said is system. If you are loaded, and have a high end system, go for it. But, most people have Sony or Polk speakers or Beats headphones from Best Buy or the head unit and speakers that came in their Honda or Chevy. Black is going to be fine and save you some money.
Not to also not mention, again, the kind of music you are playing. If low rez compressed MP3s, you don't even need a Dragonfly! A basic Fiio or better maybe, a Schiit Audio Modi or similar is fine if you need a special DAC at all. All headphone adaptors for Lightning have DACs in them. You are getting a DAC no matter what. For low end, it is really fine.
To make this even more confusing, many people think you need a DAC with Bluetooth to make it sound better. Eh, that is not how it works…
Anyhow the type of DAC chip (now so common and cheap, it is more like a commodity) is less important than the over all design of the whole unit, especially the analog portion of the process.
The need for DAC pickiness is overrated. The bigger problem is that, if you get a DAC, how to get it to work right with that Lightning slot. I am still waiting for a Lightning to 3.5 Aux DAC, that eliminates the need for various USB adaptors, some of which don't work or work better than others… See the Audioquest Dragonfly page at the bottom for more on which adaptor for Lightning is the right adaptor.