I tried on the Roon forum, I will try here as well.

[The Computer Audiophile]

That’s a tough one. Rebooting obviously does the same thing (restarts Roonserver), but at a different time. It seems like roonserver is loading before something else it requires or part of loading roonserver does something that can’t be done at the time it loads at boot up. 
 

Have you checked the Roon logs to see what happens at initial load?

 

Are there any related logs in /var/log?

[The Computer Audiophile]

33 minutes ago, AudioDoctor said:

 

headless, but with a monitor attached so I can do CLI stuff there if I need to. I am still learning at this.

 

networkmanager.service is the network manager?

Just configure ssh, then you can get to the command line from your computer, tablet, or phone. 

[The Computer Audiophile]

8 hours ago, AudioDoctor said:

Luckily my CAPS isnt a NAS.

CAPS20 runs Roon better than anything on the market 😀