In the end it’s what sounds best to you! Nice choice on the dac- I hear they are wonderful.
My streamer will upsample as well but to be honest I have everything set to Native in my system. I prefer to run AES to my dac so everything stays native at or below 24/192. If I want to go true DSD I playback native from my MacBook Pro via usb- I haven’t even bothered with trying to stream DSD.