After a few days of stumbling around, I've identified and created a patch to the mkchkimg.c file that solves my issue with installing on a fresh from the box Netgear (r8000) Nighthawk X6.
Summary:
The 'reserved' bytes are a build-stamp which encodes the version of the firmware. OpenWRT's values for these bytes appear to be too low and the .chk files are thus rejected by higher-versioned factory firmware.
My patch is to set these to a decimal of 1.9.99.99.99.99.99 which worked for me on my device allowing installation via the factory firmware's standard upgrade management page.