Well have this very same problem.
Doc 2 USB-C to HDMI picture comes to HP Pavilion 23xv - occasionally. Plug the cable in plug it out and if I am lucky I see the picture.
My hw is Surface 7 pro I7, if I connect the cable to the surface I can see the picture.
Now I am planning to upgrade to Samsung LC34H890WG, that has a USB-C.
This should work - or? Dont fancy buying an expensive screen that does not work with doc2 and 7Pro.
Any guidance is welcomed.
Jussi