Get a USB hub (7 port is common), plug the USB drives in, then run a script that copies the iso to one drive after another. USB itself sucks enough that trying to do them in parallel is likely asking for trouble.
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I have done a similar thing in the past, but to flash firmware onto any device with a certain USB descriptor that gets plugged in. It was a mess of USB hubs and cables, but it worked.
What I did was write a udev rule that checks for the vendor and product id of a newly plugged in device and calls a script when there's a match. The script then performs the flashing and logs the output.
In your case:
dd
the source USB to a file (make sure the partition you're dding is smalled than any target drive- Udev rule according to your needs (all the same product or different drives?)
- Script that dds the file you created earlier back to the newly plugged in drive.
Edit. Did this on a rpi3
Since you asked for windows, etcher can do multiple drives as of v1.4.3
https://blog.balena.io/etcher-now-with-multi-write-and-compute-module-support/
If you use a raspberry pi for each USB device, you could use multicast to distribute the iso across the network once and have each pi write it to the USB drive connected locally.
I also had a quick look around and found this:
One other idea I came across was to setup the devices as a raid array and write to the raid device.
Does your windows machine have WSL? I would just write a bash script that would DD the image to the drives. Keep in mind that you will be severely bandwidth limited by the USB interface, so it will take a long time. All of the ports on the controller share the same bandwidth. Ideally you would build a PC with lots of USB controller cards for that.
Is that true? I thought that pairs of USB-A ports shared the same PCIe lanes, and USB-C each got their own set?
Edit: thinking about it a bit more, I suppose it could depend on how the SOC/chipset allocates those lanes, but in my experience when writing a single USB I'm usually limited by the thermals of the USB, and writing well below the speed of the port. I suppose if you were writing many at once (or if your USBs were nice) that could bottleneck on the port speed.