I was in your shoes a number of years ago, kind of daunting to make the right decision!
What type of music do you listen to? Do you prefer a more warmish analog sound or prefer tons of detail? Part of system synergy has to do with luck, getting a sound complimentary to what you already have, but you don't have the luxury to try out multiple units.
On my end, I ended up with a used Border Patrol dac, because I prefer a more analog sound, using that with a used Innuos Zen mini streamer, both around $1000 each used.
I would suggest buying a used or new Wiim Pro ($149 Amazon) to get your feet wet. It is a streamer and dac. I have one for a second system (or spare) and it works great. It also allows you to add a different dac, bypassing its internal one. Once you are used to it, figure out what type of sound you want from your dac (detailed, analog?) and move up according to your budget.
Good luck!
Man, Ric, that Border Patrol looks sweet! I am definitely considering that, tho seeing the PS Audio that went for 6k, at 1600. Man.
I lean toward the warm sound and I think that complements my tube gear. As to music, I guess I'll list a few songs I really like, for some sense.
Grisman/Garcia Pizza Tapes - Knocking On Heaven's Door
Grover Washington Jr. - Aubrey
Cat Stevens - most anything off Tea for the Tillerman, Teaser and the Firecat
Julee Cruise - Falling (incredible vocals)
Grateful Dead - too many to mention! Scarlet -> Fire, Eyes of the World, just a lot, realizing not the best quality. My favorite band, all in all.
Kenny Burrell - Midnight Blue
Fleetwood Mac - Landslide (strings are incredible, with a good sonic envelope)
Bob Marley - Legend, such as Exodus
Vince Guaraldi Trio - My Little Drum (very possibly my favorite song)
Nick Drake - Northern Sky
I suppose at a high level, a former rocker whose preferences have softened and widened.
Of course, I am always up for suggestions!
By the way, I loved Supertramp Crime of the Century but somehow it sounds like crap on my stereo