TS for remote management only is not really TS. You are only allowed 2 log-ons at any time (administrative-management logons). In order to set up TS for more than 2 users you will have to turn on "proper" TS.
As to your VPN question, if your users are logging into the server via VPN, using their home desktop, then TS is not necessary. However, there are security concerns because their desktop would need to be allowed on the network, and you cannot control if they surf in personal time and get viruses etc. If they have company laptops, it's mildly better, but they still have to connect to the internet somewhere before initiating a VPN session.
VPN and TS are totally different, and in fact many roaming employees use a VPN connection to acess their TS server.
Why? Because Terminal Service users are actually using the Terminal Server, not their local desktop (laptop). What they see locally is just the "image" of the desktop sent from the Terminal Server. This means that users do not suffer too much because of a slow connection (through the VPN for example). Using only VPN to connect to the network, they will be using their local machine to process documents and things off of the network, and so every time an update is required, it takes ages to go over the link. If you have broadband it's not as bad, but still not as good as connecting to a Terminal Server which has 100MB connection straight on your network!
We also worry about cost, and at my company I use an Open Source solution to connect to our network securely over SSL (Secure Sockets - You access using https:// instead of
All a user needs is an Internet connection and Remote Desktop client (RDP). This is NOT VPN, but is very secure. It is easy to set up:
SSL-Explorer
We do have a Terminal Server with 20 CALS (you can get them in 5 person/device increments - I suggest you get User CALs for a small organisation. Device CALs are good if you have single machines that serveral users use to access the same Terminal Server, like a Mainframe).
In short we connect using SSL-Explorer through the Internet, and then launch RDP (TSClient) using SSL-Explorer (built in function which makes it cool), and access Terminal Server.
I hope this helps. If you'd like any more clarifications, let me know.
Will