You will have the option to switch between the 2 DACs
only if your Rasp-pi DAC has a digital output (S/PDIF or TOSLINK)
Regarding the headless equaliser:
- I will assume that you have a Linux box or a Raspberry Pi with a desktop install. I suggest you develop the EQ on the desktop and then port it to the headless system.
- Room EQ Wizard (REW) is your friend. You can measure EQ through a 2nd laptop + 2nd interface, or you can measure EQ by routing the signal via (pulseaudio) pavucontrol or qjackctl.
- Create the eq config file on the desktop, configure the ALSA plugin, measure with REW.
- If you are using 2 devices: you can export the sweep (or the pink noise) to a wav file, and play that on the "playback" system.
- Note that REW can generate a freq. response plot from EQ settings, or import a freq. response from a csv file. You can then compare the expected EQ with the measurement.
- Be patient, REW is a "big" application, there is a lot to learn. You can start by measuring "trivial" EQs
I hope this helps. I apologise if you already use REW and know all this.