First thing, do NOT go out and spend a boatload on gear. Start slowly and get to understand how streaming works and what you want it to do. Consider Roon as there is a good community to help you get up to speed on how to use it.
Second, do not apply analog logic to digital gear. Lots of the tweaks and boxes and audiophile widgets on the digital side are of questionable effect (to put it mildly). Another reason to learn before you dive in.
Third, even a relatively cheap DAC (understanding that is relative - I mean those sub $1000, some of them well below $1000, have 98% of the performance of more expensive DACs. So make sure to get a decent one to start but you don't need to go higher until you know exactly what you want, if you ever do.
Qobuz and Tidal are the lossless streaming providers that work with Roon. Suggest you start with one of them - Tidal being easier to use.