FreeRDP

FreeRDP provides a Windows Remote Desktop client.

You’ll probably need Windows VMs, including old ones. You may be interested in https://archive.org/details/modern.ie-vm and https://developer.microsoft.com/en-us/windows/downloads/virtual-machines/

Basic testing for W7:

xfreerdp /v:192.168.122.41 /u:ieuser /p:'Passw0rd!' /sec:rdp

USB testing (/usb:id,dev:XXXX:XXXX with XXXX from lsusb):

xfreerdp ... /usb:id,dev:0781:5581

Note: to share USB devices through a VirtualBox Debian VM (so you can share them to e.g. xfreerdp/stretch), you’ll need your main desktop user to be in the vboxusers group.

Directory share testing (test both reading and writing):

xfreerdp ... /drive:myhome,/home/myaccount
# access it through \\tsclient\myhome
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