You have chosen a good time to add a digital end. I have been trying to get digital to sound as good as analog for… well since digital began. A few years ago I was finally able to do that. You can see my systems under my ID.
Great idea of one and done. Has that ever happened with analog? Ok, anyway.
Definitely Aurender streamer and a good quality DAC. Knowing nothing about your preferences I would say an Aurender N250 and an Audio Research DAC 9. Good combination of great detail and musical. An Aurrender N20 would be even better, but that would be over your budget.
Streamers and DACs are equally important, so both must be good quality. If you could get a used N20 and a used high quality DAC you could be in business. FYI, I found equal sound quality between my analog leg and digital required carefully chosen components for each leg which ultimately cost the same… $ analog leg = $ digital leg.