I've been swamped at work and I've finally had time to sit down and do more testing. I've had a bit of a breakthrough. I updated my MB to the latest beta BIOS and now my monitors are detected at boot. This has been a big hurdle and confirms the main issue has been local. While the config of DP to GPU and one pass through over TB is working consistently, I'm still trying to get to both monitors over TB. I share my workspace with a rMBP and if I want to work off the laptop with my monitors and dock, I would like to just plug in one cable and be done. Also, I am using the THB_C header.
After many different tests, CSM is definitely a problem and needs to remain disabled. I have had some success booting with both monitors running over TB, but it never survives a reboot. The machine boots to the desktop, but remains black. System profiler sees all TB devices including the UltraFine monitor and all of its properties- Sound Options, USB ports... but under Graphics/Displays- nothing. I started reading up on WEG to see what options are available, and documentation there suggests CSM is a problem for multiple monitors, AND defining ports and connectors of the GPU can help with black screen problems. I am becoming more and more convinced that it is in fact an issue with my Radeon VII and detecting ports/connectors and their priorities. This would make sense as your Vega 64 has better support in MacOS. So what I'm wondering, is there a way to inject these extra properties into Clover or perhaps the Radeon Boost SSDT? This might prevent WEG from detecting (incorrectly) priority of the ports and connectors.
Also, is there anyone willing to help me do this?