One common error folks make with SBS is NOT using the "Add Server" Wizard in SBS's Server Management.
I have no idea what this does, as I do not recommend SBS for my customers, but that is a rant for another time. That said, I can only assume that it joined that server to the domain. To check this go to: system properties> computer name, and then see if it is in the domain. It should read something like "servername.yourdomain.local". This same place would say if it was only in a workgroup.
It's easy to forget and manually join the additional Server to the SBS Domain.
I've done it manually numerous times with no issues. But then I do not need a wizard to configure servers.
So, go to the TS machine, log it onto the SBS domain as Administrator and that should "synch" the 2 user lists
Sort of... yes. It enables the domain user and group objects to be recognized when you go to add the user group to the TS.
They are all just part if the default "users" group
Some SBS servers put the users under a Organizational Unit named something like "My Business", not under the default users. In the end, as long as you find where the users are, it "shouldn't" matter. I have seen some odd permission restrictions when the users were in the default users group. As part of setting up a server now, I always create a new Organizational Unit and place the users there.
Where is the logon script located?
The reason thay are not getting the script to run is because they are using the local user account credentials on the TS that you created. User logon scripts do not run when you logon to a member server. When you add the domain user group to the Remote Desktop Users group on the TS, and you have the TS logged on with a domain account, such as the domain administrator, then the script will run because they are validating with a domain account.
Just FYI, the reason I'm actually adding this TS is simply for a small, remote office so they can access some databases, programs, files etc and so that when employees are traveling they can access the network.
How are they going to access this over the internet!!?? Are they going to be using VPN software to a firewall to encrypt the traffic? Do they have a VPN between the two offices? Hopefully they are using a firewall, and not just a plain router. How is the RDP going to be redirected in? If all internet RDP traffic is forwarded into the server, instead of being narrowed down to be allowed only from the remote office's IP address, then they better have some strong passwords, as anybody could try and logon on. If they are going to access this from the internet, there is a setting to make RDP only use 128 bit encryption instead of 40 bit.