The server does not need an outward facing IP address.
If you're connecting by VPN, you're already local, so there is no
need for an outward-facing IP address.
That is, unless your VPN is not a direct connection to the LAN you
need to get to. In that case, though, I don't see how you're getting
to the workstation, unless there's some form of IP or port
redirection on the Internet-facing router.
All connectivity is
behind the router and firewall. So the only way in is a local
terminal session, or a local login to the server. Anyone probing
IP addresses will never see the server, and only sees a
workstation. Had I a permanent IP from which to start the Terminal
Server session, I could have set up the server to only accept 1 IP
address from the outside. This way it only accepted 1 IP address
from the inside.
If connecting via VPN, I can't understand why you would be worrying
about external IP addresses. The whole point of a VPN is that it's a
secure tunnel to a protected port available on the Internet. Once
you've connected, the usual configuration of a VPN is that you now
have an IP address local to the inside of the LAN, and have all the
LAN addresses available to you.
And your explanation doesn't account for how you get to the
workstation from outside the LAN.