Not related to selfhosted but OK.
Don’t know about such software for Windows, but if you run Windows on a virtual machine on Linux, like virt-manager/libvirt you can add the USB as a local SSD.
Virt-manager isn’t the most user friendly, but have a lot of features
Not here, i use it regularly for updates and install some apps. Just checked and updated some apps.
PS: I’m using a created account.