@mattmiller
Roon is a software just like Conductor but much more advanced and also not without its complexities. @duckworp summed it nicely for you but here is the thing, if you find yourself struggling using Roon, then all of its virtues not going to matter.
Also, Roon requires minimum of two devices (hardware) for best sound quality, one device called a server to run its core (brain) and the other a streamer, often termed as renderer. A general purpose PC or MAC can serve as Roon Core and there are limitless options for Roon endpoint (renderer).
In contrast, Conductor app is straightforward and robust. I am a long time Aurender user and also a Roon users for about three years now. I still prefer Conductor app by a mile for its simplicity and sound quality. And as you know, Conductor is equally adept at managing your library. Other may disagree with my assessment on Roon SQ but it really comes down to its implementation and your choice of gear to extract the best SQ from Roon.
If you value simplicity and convenience, then Conductor is the way to go!