Yes, error 74 can be ignored. And please feel free to share videos of the LED to confirm that your Daisy has bootloader on it or not. It should be slowly glowing.
And just to recap the steps:
With your Daisy in the physical world, put it into bootloader mode (DFU in FS Mode) as usual by press and hold boot, press and hold reset, let go of reset, and let go of boot.
Then flash the Daisy bootloader to your Daisy!
Next, press and let go ‘reset’ and then press and let go ‘boot’. You should see your LED breath or slowly glow and fade repeatedly. This indicates that Daisy bootloader is ready.
Finally, you flash the program using the Daisy bootloader.
And as far as I remember, you do not need to flash the Daisy Bootloader Image every time.