Hi,
Had similar issues, I connected Surface pro 7 to Surface dock 2 through to 2 x AOC QHD 32 inch monitors I used 2 x usb - C to HDMI cables. I could get the monitors to turn on and function by plugging and unplugging the cables in a specific order. This was of course frustrating and not ideal given the cost of the set up. The problem was fixed when i ditched the usb c to HDMI cables and put the HDMI FEMALE to usb C MALE adapter in place for both monitors and connected to the monitors with the HDMI cable that they came with. Now it works perfectly I can unplug the dock and plug it into any surface and both monitors come on as they should.
Hope this helps