Hi @laramsey. In my opinion, the OpenOCD approach I described is easier.
However, if you are also using the proprietary tools provided by Segger for applications other than debugging the GIGA R1 WiFi board via Arduino IDE, then the debug_custom.json approach described by @KurtE here (with this modification applied) will be best since it might be that the Segger tools won't work with the WinUSB driver that is used with the OpenOCD approach.