Ventoy makes reinstalling operating systems or testing Linux distros much easier.
Install Ventoy once, then simply copy ISO files to your USB drive, no need to reformat it every time you add another image. It also supports multiple operating systems, Secure Boot, persistence, and many rescue tools.
GitHub: https://github.com/ventoy/Ventoy
More details: https://digitalescapetools.com/tools/tool.html?id=ventoy
More privacy-friendly tools: https://digitalescapetools.com/
with a ventoy usb stick, all you have to do is copy bootable .iso over. that's it. you get a menu at boot to pick one.
it's extremely convenient.
This is the main reason I use Ventoy.
I have a small external drive and I just dump multiple ISO files on it and then select whichever one I want at boot, I don't have to keep formatting and making new bootable drives.
It does mean you have to repackage isos if you want to include/update files.
For example, it made an automated.xml file for windows install a lot more complicated. But now I have a very nicely scripted iso builder for customised windows installations (I work in the events industry, so things like digital signage and show machines can be 95% configured before I even have to interact with it).
It's still windows, but it's now hands free from iso boot to being able to use it with the software and settings I want.
Ventoy, as far as I know, uses image files only, so if you are making changes to your files then my best guess is you will need to update the ISO or rebuild it.
I mainly use it for distro hopping, I will download the latest version of a Linux distro to give it a try. Got quite a few on my bootable drive. So I never update any files other than replacing the ISO I had been using for a certain distro.
I think Ventoy would work in your case if you needed to carry around more than one version of the automated Windows install you are using.