I've also tried Roon for a few days and decided to cancel my trial way before the period ended. Here's the feedback I gave to them, based on what I saw it doing (or not doing) to my music library:
"The tagging still have a long way to go to be close to ideal and justify the costs.
Two good examples of what I am saying: you categorise the Brazilian artist Chico Buarque as bossa nova. He's not a bossa nova musician. Then I removed the tagging, but his albums are still marked as bossa nova. So, removing the tag from the artist does not remove the tag from his albums. These are two tagging failures in one example.
Secondly, the violin player of Dave Matthews Band, Boyd Tinsley, is only associated with one of the band's album, although I have 54 albums of the band and he has played in all of them. Very upsetting!
Another problem I have is that it doesn't seem to be possible to organise albums by audio resolution. I have flac and DSD versions of the same album, I'd like to be able to know before selecting the album which one I'm choosing (these are separate masterings of the same album, by the way, reason why I want them both there).
The software is an effort that I can appreciate, but you are really aiming too high with that price mark in my opinion. Spotify or Apple Music leaves you in the dust in terms of tagging accuracy, I'm sorry to say. And music quality aside, I can listen to 30,000 songs anywhere with a subscription to one of these services. With Roon I have to buy a subscription to keep my own purchased music files (or Tidal) presented in an interesting way, but this is failing in my opinion. For a fraction of the cost I could probably bear with the amount of extra work I'd have to do with Roon to give full meaning to categorisation or my music library. There's no way I'm spending the asking price to do half of the work myself."