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No pedal attached yet.Output level is a different issue from impedance. But amps get damaged from driving too little impedance, not too much, and the line input of an amp would be high impedance. So plugging into that amp from a headphone jack would not damage the headphone output. But while connecting a headphone out to an external amp won't damage the headphone out, you'd want to keep the keyboard volume quite low so as not to risk overloading the input of the amp (or sending a signal that could blow its speaker).
But anyway, there is no reason one should need a mixer to get a usable level of sound out of the DS, and it certainly wouldn't affect the level of the DS' headphone out.
Just a thought... do you have an expression pedal plugged in, which may be lowering the volume? That would be another thing that could result in lower volume through the main outs and the phones... though it wouldn't explain any distortion, nor your faint beeping sound, so you have something else going on regardless.
Both sounds that I’m having issues with come via usb - from a stick and usb MIDI from the pc. This would be the common denominator, I guess..