The product intent is that you do not worry about this stuff at all–because most people on Earth do not worry about this stuff at all. Your friend is doing it right with his sloppy library
It’s a good long-term bet that software will get smarter about this, not dumber. Roon is a lot more capable of dealing with the messes that humans make than the things that came before, and I’m sure we won’t be the last to take steps in this direction (nor will we stop working on it).
Roon is all about automating metadata cleanup.
If there are particular things we’re not getting right repeatedly, we’d really like to take that feedback and improve. The idea is, you should be able to drop your files in and get a good experience for almost all of it, and perhaps do some small tweaks to fix the rest if it is annoying you.
My music folders are totally unorganized, like your friend’s. They follow 2-3 different inconsistent formats from different periods in my history of collecting music. About 30% of my library is a raw database dump from Sooloos that is totally incomprehensible to humans and mostly void of file tags. Even in this situation, Roon makes decent sense of 90% of it.
The only editing features I use are:
- “Merge Albums” if for some reason Roon can’t put a multi-disc set together
- “Merge Artists” (I’ve used this 9 times)
- Adding artwork if it’s missing
I touch file tags or directory structure perhaps 2-3 times per year. It’s so rare that it is barely a consideration.
I don’t care, because I’ll never move to something that isn’t as good at handling my messy library as Roon is.
Comprehensive editing features, detailed documentation about directory structure, etc, is for the subset of our users people who treat music metadata grooming as a hobby or who cannot tolerate a statistically tiny number of mistakes in their music library. If that’s not your hobby, this stuff is best ignored.
A long time ago @AndersVinberg made a great post about this that I can’t find anymore where he laid out the tradeoff: Roon makes it so you can spend almost 0 time/effort on metadata cleanup and enrichment. In return, you tolerate a small level of imperfection. This is pretty much how all automation of previously human activities goes. Computers are good at different things than humans are, so the results are different. Maybe Roon doesn’t get every box set right–but there’s a 0% chance that I would ever go hunt down biographies for every artist in my library manually.
@ncpl once shared the story of how much labor was involved in bringing his huge library into Sooloos (which required individual confirmation of each Album’s metadata upon import), whereas Roon can do it overnight while he sleeps.