Hey
@Thackeraye I am like you, I have tons of bootlegs (Bowie et al). There is no additional metadata for Roon to pull from AllMusic. But you can add genres within Roon (does not alter the IDtags). You can categorize within Roon by indicating album is LIVE and it is also a BOOTLEG.
You can also create tags (these function outside genres). So I have a tags like BOWIEBOOT, MOGWAIBOOT, etc so I can see them easily all in one spot. Even though Roon has a Live category, I also used a tag called LIVE for any bootleg.
Also it reads your folder names in an interesting way using brackets and parenthesis. So this is the folder name I have as an example for a Bowie boot. I use the [ ] for a lot of different information
1999 - Eternal Life [Paris Bootleg]
Paris Bootleg will display on the information screen when you are playing, just under the star rating. I will try to remember to do a screenshot when I get home this afternoon.
So the short answer is that with a little work on the backend, Roon handles bootlegs really well.