Hi,
You need to contact the software vendor and ask them how it needs to be set up/configured to be compatible with Terminal Services/Remote Desktop Services. In your previous Citrix environment they were likely using a compatibility flag and/or some sort of virtualization technique and/or similar method to allow multiple instances of the app to run on the same server.
Another alternative is to analyze the application and determine the method(s) it is using as it relates to the error and then based on that change how you have things configured. For example, figure out how it is checking that "device is already logged in to MatchMaker" and then you can come up with ways to work around it.
Many years ago it was somewhat common for multiuser software to use the hostname of the PC it is running on, and if more than one user tried to start the software with the same hostname it would fail. In an environment where each user has a dedicated PC, this is okay. In environment where multiple users are sharing same PC (Terminal Server, RDS, AVD multi-session), this is not okay and may be resolved by compat flag.
-TP