Help Next Step for a Noob

Well I read a lot about how good Tidal sounds but I'm content with Pandora & Amazon Prime Music...I also read how converting to Flac files also sounds better but you must need a $100K system to hear a difference cause mine modest little rig doesn't show one...I think if anything is weak in your rig you would notice either  hard/steely treble,one note bass,uninvolving midrange or a combination of all...I also note when streaming that jitter problems cause a lot of dropouts so if your signal stays locked & strong then that probably isn't a problem either..What you really need to do is figure out how your rig really sounds,from there changes or upgrades are much easier...Good luck...
PS:When was the last time you heard live,unamplified music?Without that it's hard to judge your sound...

Roon is one option that can be used interface between your music collection, online music such as Tidal, and your DAC. JRiver is another software many prefer for this function though Tidal is tricker to use. Both can run on a windows platform.  

tomask6 - My understanding is that there are better ways to play the content besides iTunes.

I'm not certain my suggestion would be "better" than iTunes, but if it's an alac m4a file and you're using windows 10, what would be wrong with using windows media player, already included with the OS?