At on of our customers we ran into a simular issue. After investigating the logs we found that if the user logon took more than 60 seconds the USB redirection was not working. With logon times less than 60 seconds everything was working fine. Disconnecting/connecting the USB device resolved the issue.
After setting this reg key our problem was solved. The 60 second timeout is increased to 200 (max)
[HKEY_LOCAL_MACHINE\SOFTWARE\VMware, Inc.\VMware VDM\USB]
"WaitForSessionIdTimeout"=dword:000000c8
For more info take a look at this kb:
VMware Knowledge Base
Roderik de Block
Blog: https://roderikdeblock.com