So I'm just using the headphone output of the DAC2 Pro, when I plug headphones in it works great, once I unplug the headphones I cannot get any audio out of the headphone socket again until I reboot the Pi (restarting the audio, changing audio settings, etc. don't work)
I'm pretty sure it's related to physical detection of the 3.5mm jack as I put a small extention cable in and I can unplug and replug my headphones from the extention just fine.