Hi Joshua, I have the same issue where the screen (1 of 3) plugged in to the USB-C port fails to initialize unless unplugged and re-plugged in, while the laptop is connected. The two screens connected via HDMI function without issue on startup. I also noticed, similar to hcanning that one or more screens defaults to run off my computers native USB-C video capabilities, even when only the two HDMI screens are functioning, and not the DisplayLink chipset. This is a personal laptop with all Windows and manufacturer (Lenovo) drivers/software updated. I will email the plugdebug file to support@plugable.com for your review. Looking forward to hearing back. Thanks.
With the three monitors detected (after unplugging and re-plugging monitor #3):
Note: this issue (and the plug/unplug fix) is also replicated exactly the same with a new Macbook Air, indicating that the issue is localized to the docking station, not the computers.