I had a problem installing client based USB locally connected printers onto a Terminal Server, especially the HP All in one printers.
You can have issues with the install on a server, it can kick off DEP, not install or some other idiotic issue.
To get around this I do the following;
Start the installer.
Open Sysinternals Process Explorer http://technet.microsoft.com/en-us/sysinternals/bb896653.aspx
Stop the install and then use the copied out folder for the install of the printer onto the Terminal Server.
Bingo - all sorted.