What kind of dication software are you using if I may ask? We tried doing this with Dragon but because you can also control the machine itself with it this did not really work all to well because it needs to be there before the machine starts.
That being said. I'm trying to figure out what you are trying to do. Do you have the use case where 1 users needs both applications but just on a different machine? If so couldn't you create 2 groups, and when assigning the appstacks make sure to do a machine prefix assignment? Computers on both parts do need to be in a different pool for that off course and the prefix of the machines do need to be different.