I’m afraid you have to play a little with manual set the display resolution via cmdline.txt. The newer kernel versions are very sensitive to the EDID data. In combination with your VGA adapter, these could be missing or may be incomplete.
Within the case, the power is supplied via GPIO pins, not via the USB-C. That could cause a difference in timing while switching on.
Try to append this to the kernel line in the /boot/firmware/cmdline.txt video=HDMI-A-1:1280x1024M@60D