Cognizenti,
Here's my first question: would the SQ improve if I replaced the stock output caps with larger, higher quality caps?
If so, can I bypass the resistor and further improve the SQ?
earplay
A better cap probably would help. I did have a tube preamp once, where upgrading the coupling caps did not help it, but after I upgraded the power supply, then the coupling caps were an improvement.
IOW, depends are the quality of the signal going into the caps. If the DAC is generating a reasonable output, then upgrading the caps should get you closer to hearing what is coming out of the DAC. A higher value may not be necessary, the higher value will lower the frequency of the signal getting through, but if it is low enough already, then an higher value cap does not buy anything, and might even hurt. They would be larger, and harder to install.
I would not bypass the resistor unless I know what it was there for. Normally, people put in resistors for a reason, and it's not a good idea to short one out, unless you know what you're doing, and how it will change the characteristics of the circuit.
Randy