I opened a case with them and they had me install "Capture_Data.dmg" which allows me to reproduce this issue and gather all the necessary logging.
Being the curious person that I am I started to review the logs that I captured from the Apple "Console" app built into the OS.
One of the things that I saw over and over again was this message:
[ERROR] - Attempting to get capabilities from capabilities with no devices
Here's a sample from my logs:
default 2022-03-14 16:57:02.478312 -0400 USBCAccessoryUpdaterService com.apple.mau.plugin.usbcupdater.USBCBillboard-VGA with S/N REDACTED is up to date. Installed firmware version is 2.35.0
default 2022-03-14 16:57:02.478390 -0400 USBCAccessoryUpdaterService validateUSBCBillboard gave: Error Domain=USBCAccessoryFirmwareUpdater Domain Code=8704 "(null)" UserInfo={Previous Error Response=Error Domain=USBCAccessoryFirmwareUpdater Domain Code=9728 "(null)" UserInfo={Notes=Firmware not new enough}}
default 2022-03-14 16:57:02.478470 -0400 USBCAccessoryUpdaterService validateDevice has an error: Error Domain=USBCAccessoryFirmwareUpdater Domain Code=8704 "(null)" UserInfo={Previous Error Response=Error Domain=USBCAccessoryFirmwareUpdater Domain Code=9728 "(null)" UserInfo={Notes=Firmware not new enough}}
default 2022-03-14 16:57:02.478674 -0400 USBCAccessoryUpdaterService -[USBCAccessoryFirmwareUpdater initWithDeviceClass:delegate:info:options:] - returned error: Error Domain=USBCAccessoryFirmwareUpdater Domain Code=13568 "(null)" UserInfo={Previous Error Response=Error Domain=USBCAccessoryFirmwareUpdater Domain Code=13568 "(null)" UserInfo={Previous Error Response=Error Domain=USBCAccessoryFirmwareUpdater Domain Code=8448 "(null)" UserInfo={Previous Error Response=Error Domain=USBCAccessoryFirmwareUpdater Domain Code=8704 "(null)" UserInfo={Previous Error Response=Error Domain=USBCAccessoryFirmwareUpdater Domain Code=9728 "(null)" UserInfo={Notes=Firmware not new enough}}}, Notes=Failed to validate connected device: com.apple.mau.plugin.usbcupdater.USBCBillboard-VGA}}
default 2022-03-14 16:57:02.478792 -0400 USBCAccessoryUpdaterService Entering: -[USBCAccessoryFirmwareUpdater attemptErrorRecovery:delegate:]:440
default 2022-03-14 16:57:02.478902 -0400 USBCAccessoryUpdaterService Disabling lock (does nothing)
default 2022-03-14 16:57:02.479017 -0400 USBCAccessoryUpdaterService -[USBCAccessoryFirmwareUpdater attemptErrorRecovery:delegate:] - VerifyEmptyPortAndReset gave: (null)
default 2022-03-14 16:57:02.479125 -0400 USBCAccessoryUpdaterService Device of type com.apple.mau.plugin.usbcupdater.USBCBillboard-VGA did not meet requirements for update
default 2022-03-14 16:57:03.564440 -0400 WindowServer [WARN] - IOFBSetDisplayModeAndDepth: Setting mode 0x80004000 with depth 0x2 on displayID: 0x0 fbRegID: 0x100000767
default 2022-03-14 16:57:03.564443 -0400 WindowServer [WARN] - IOFBSetDisplayModeAndDepth: IOService:/AppleACPIPlatformExpert/PCI0@0/AppleACPIPCI/PEG0@1/IOPP/EGP0@0/IOPP/EGP1@0/IOPP/GFX0@0-4c2d-a00-144a1f77d977c55
default 2022-03-14 16:57:03.831429 -0400 WindowServer [WARN] - IOFBSetDisplayModeAndDepth: Mode has dimensions 1920x1080
default 2022-03-14 16:57:04.144445 -0400 WindowServer [WARN] - IOFBSetDisplayModeAndDepth: Setting mode 0x80004000 with depth 0x1 on displayID: 0x0 fbRegID: 0x100000769
default 2022-03-14 16:57:04.144448 -0400 WindowServer [WARN] - IOFBSetDisplayModeAndDepth: IOService:/AppleACPIPlatformExpert/PCI0@0/AppleACPIPCI/PEG0@1/IOPP/EGP0@0/IOPP/EGP1@0/IOPP/GFX0@0-4c2d-9ce-86fa915750445fad
default 2022-03-14 16:57:04.147804 -0400 WindowServer [WARN] - IOFBSetDisplayModeAndDepth: Mode has dimensions 1920x1200
info 2022-03-14 16:57:06.748636 -0400 WindowServer Warning: Unable to acquire capabilities for 0x10000076b:0x1000008c0:0x100000764, return code: 0x2006
error 2022-03-14 16:57:06.748641 -0400 WindowServer [ERROR] - Attempting to get capabilities from capabilities with no devices
info 2022-03-14 16:57:06.748711 -0400 WindowServer Warning: Unable to acquire capabilities for 0x100000774:0x1000008c0:0x100000764, return code: 0x2006
error 2022-03-14 16:57:06.748714 -0400 WindowServer [ERROR] - Attempting to get capabilities from capabilities with no devices
info 2022-03-14 16:57:06.748819 -0400 WindowServer Warning: Unable to acquire capabilities for 0x100000705:0x100000740:0x100000700, return code: 0x2006
error 2022-03-14 16:57:06.748822 -0400 WindowServer [ERROR] - Attempting to get capabilities from capabilities with no devices
info 2022-03-14 16:57:06.757074 -0400 WindowServer [INFO] - Found 430 modes for display 0x04281106 [430, 0]
info 2022-03-14 16:57:06.758641 -0400 WindowServer [INFO] - Found 430 modes for display 0x04281106 [430, 0]