External display wakeup problems have been an issue on many generations of MacBook Pro going back to PowerBooks (even with Apple displays). Very annoying!
The fix was to use a USB-C -> DisplayPort cable (using DisplayPort via USB-C alternative mode). It appears that the HDMI port can't be used with a DVI converter. DVI ports have been replaced by DisplayPort, HDMI, and DisplayPort for some time but it was still a disappointment.