@delnwyr and @pholgate
The latest version of dnd5e (2.2.0) mainly has fixes for v11 and has been reported to cause some issues in v10, and I’m not certain if these persist into v11. My recommendation is to roll back to dnd5e 2.1.5 over here The Forge and to Stop and Start your server at The Forge and stay on Foundry v10 at the moment.
That should get things functional again.
Remember to take a backup before updating versions if you plan to update to v11 instead!