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/
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.