Hi @EmbeddedTech,
In this case, if you want to use the iMXRT1060 as Mass Storage Device a secondary bootloader will be necessary in order to support this feature.
We have the AN12604 Implement Second Bootloader on i.MX RT10xx Series and the AN13497 Firmware Update Using Secondary Bootloader that you can use as reference, however the implementation of MSD should be made on your end.
Other option could be to use a software such as MCUBootUtility in order to do the updates, the official tool that we have is Secure Provisioning Tool.
Even though this software does not have the option of drag and drop, you are able to build and write the image through USB, just take in consideration that you will need to manually set the MCU as serial downloader. I recommend you the take a look to the training Getting Starting with MCUXpresso Secure Provisioning Tool.
If you still want to use MCUBootUtility there is a GitHub that you can take as reference
GitHub - JayHeng/NXP-MCUBootUtility: 恩智浦全系列MCU安全启动一站式工具(研发模式),基于Python2.7.15+wxPython4.0.3