The goal was to share a USB Xbox 360 Wireless Receiver over RDP. I wanted to plug into Laptop and share input on VM hosted on powerful server. Turns out its overly complicated in Windows 10 to enable, not so much in older Windows, but it is doable.
This could be used to share a multitude of USB devices though!
The software/feature is called RemoteFX USB Redirection.
To Enable it:
Do on both Physical Windows Machine and Remote Host
All edits are under the following:
Computer Configuration \ Administrative Templates \ Windows Components \ Remote Desktop Services \ >>
Remote Desktop Connection Client \ RemoteFX USB Device Redirection \ All RDP Redirection (Enable)
Remote Desktop Session Host \ Remote Session Environment \ RemoteFX for Windows Server 2008 R2 \ Configure RemoteFX (Enable)
Remote Desktop Session Host \ Connections \ Allow users to connect remotely using Remote Desktop Services
Remote Desktop Session Host \ Device and Resource Redirection\ Do not allow supported Plug and Play device redirection (Disable)
In elevated CMD Prompt and then reboot
Using the Feature in RDP:
Open RDP >> Show Options >> Local Resources >> More >> Other Supported RemoteFX USB Devices >> (Enable Device to share)