Hey Scott.
Thanks for commenting, it's been a little while since I wrote this article and I'm sure things have changed since then.
1) I adjusted the article to include "Create the key if it doesn't exist"
2) On the program you want to route out of the WireGuard interface, have you told it to use the WireGuard interface's IP? I haven't tried ForceBindIP as mentioned in the article but in theory it should work. I use Proxifier and it works great.
3) I haven't used Plex in a long time but I think it may use the default interface. See if you can force it to use the WG interface or WG's IP, or use Proxifier to tell it to use the Plex EXE. That might help. DNS could also be the culprit with this, but I'm not sure.