My new MacBook Pro 13" touch bar is connected to my Samsung Syncmaster monitor through USB-c hub -> HDMI -> DVI. It detects the screen (shows up on OSX) but nothing is displayed on my screen. I have connected the MacBook on my LG TV through USB-c hub -> HDMI and everything works.
It's most likely because you are doing two conversions of the video signal and at some point it's either being degraded and/or becoming out of sync.
The two conversions I am referring to is going from DisplayPort to HDMI then going from HDMI to DVI. In your original question, you never mention specifically what adapters you are using nor if they are active or passive.