I'm at a digital loss or getting over UI mountain

So far, I hate digital audio. Let me explain...

I was an early adopter of one of the Olive machines. Easy to use, which was a big plus for my wife but it sounded terrible. Good for some background music. As the company began to disappear, so did its functionality. First the radio left when they stopped paying for it. They stopped supporting the wireless transfer. Then, Gracenote no longer updated etc. 

Since then I tried to organize a digital collection in my Mac Mini and iTunes. I have thousands of CDs ripped in ALAC, thousands of pieces in FLAC and MP3. I carefully built a library in iTunes only to lose all the artwork in the iOS upgrade to Music recently. After the Olive, I bought a Sony HAP digital player which upsamples everything and sounds WAY better but, can't seem to categorize things correctly. All the careful work in the Mac Mini is lost in translation. 

If I look in Genre: Reggae, for example, there should be thousands of albums and yet there are a handful. There seems to be no way to alter this. Furthermore, try find albums that should be classified as Various Artists - most get lost somewhere. And don't even get me started on Classical music and its filing system. 

I usually just go over to my albums and select something to play. It never changes operating systems, its UI is excellent, taxonomy never changes, always sounds good...So why mess around with digital?

I'm intrigued with Roon and wonder if it could solve the UI and taxonomy issues but, I don't know anyone who uses it. Of course, someone just bought it so, will it be around? I can't seem to rely on Apple either although it seemed the best most stable bet. 

I've agonized on whether to get a DAC/streamer but library management is most critical to me. I have been looking at the Hifi Rose lineup as I really like the one box solution (easy to use for wife). But if I implement Roon, I still need a computer somewhere to host it. Since I already have the MacMini it seems like a good place to start. However, how to deal with all the UI stuff?

Perhaps hivemind you can help me out here?