Not with the AudioQuest DragonFly Red but the DragonFly 1.2. It works straight out of the box with Ropieee in both wired and wi-fi and is immediately seen by Roon when plugged in.
Yes I have a pi3, Ropieee and DF red and it runs on WiFi with a very large 20000ma battery. It’s solid and stable and runs as my bedroom headphone setup. It’s a good.performer, but nothing amazing but I think this is a limitation.of my headphones and the pi it’s self. As my cobalt and NuC combo sound way way better.
The dragonfly red is one of the most forgiving DACs I have come across in terms on the device and OS that hosts it and on an RPI 3B+ under Ropieee is was the most reliable I have used with an R-PI.
Of course more expensive ESS based DAC will usually yield more detail (even if they may otherwise sound almost identical sound character wise), but at it price point and for portability I think it is a decent DAC and passes the most important test of being hassle free and completely stable whatever I have plugged it into.
I mostly use mine in my car now with my iPhone with a project S2 digital being plugged directly into an intel NUC for Roon.
One additional question , does a RPi have Bluetooth or will it power a Bluetooth dongle, I am considering a pair of Sennheiser Momentum wireless or the like
It has bt built in but I don’t think it will work for Roon bridge if that’s what you want. Ropieee won’t use it as it has no bt functionality. DietPi has it in the menu but I could never get it to work myself. A usb Bluetooth dongle might work and be recognised as a device . I would just buy one and see as they are cheap enough.