What's the version of your S32DS? The Executable in Debug Configurations of hello_world_s32k144 SDK example is different from mine. Maybe you can try:${cross_prefix}gdb${cross_suffix}

Is the PEMicro software in your colleague's S32DS the same version?
Try update it Help->Install New Software.

Have you tried uninstall and reinstall the windows driver of PEMicro
?
I met a customer similar to you before, who was able to burn by throwing srec or s19 files into the MSD disk, but he was still unable to use the onboard OpenSDA to debug. Later try to switch the onboard OpenSDA to Segger J-Link to be able to debug. (press reset button and then plug USB cable, drop the attached OpenSDA_V1.bin. The PEmicro OpenSDA will be Segger J-Link)