Hi Ryan,
You are specifically using MCUX 10.1 and the interface with hyperflash is somewhat more straightforward, compared to IAR.
MCUX is using a flash driver loaded through the debugger to program the hyperflash, and you do not need to put the EVK into SDP mode with SW7 to load the image to flash.
Here is the procedure:
1) Make certain that you have a USB connection via J28, that the power jumper J1 has header 5:6, and your board is enumerated correctly by the host interface - you should see the drive EVK-MIMXRT.
2) Confirm the version of DAPLink firmware on the debugger -> open the file DETAILS.TXT on the EVK-MIMXRT drive and confirm that 'Interface Version' is at least 0244.
3) Leave boot mode switches on J7 as 0-1-1-0 : you will not need to move these at any point.
4) Compile the hello_world_xip code, you'll get an output file evkmimxrt1050_demo_apps_hello_world_xip.axf.
5) Run a debug session (use the Quickstart Panel) & MCUX automatically flashes the image... it should not take more that 5 seconds, and the image is executed up to the c-language entry point main(). Then of course you'll get debug control.
6) If you don't want to use the semi-hosting interface, you can easy modify the SDK Debug Console output to UART (I mean, VCOM via the DAPLink) with the Quick Settings>> menu in the QuickStart Panel. Obviously you will need to stop the debugger, rebuild & flash your code, and use TeraTerm, PuTTY or equivalent.
Happy flashing. Let us know how you get on.