Well that's the thing, I don't control that device. And obviously not the doctor either. All I got is that remote software installed on one office computer, by the doctor himself, and he just knows that he has to login with this program and then he can access his studies. I thought that I could configure the pfSense device to use split tunneling, or some way to trick the program into thinking that it has successfully blocked off all local IPs when it really hasn't.
I guess my brain was thinking visual like if two people shared the same glass of drink with two straws, then person 1 (Mr. Cisco) could drink from his straw while person 2 (Miss LAN) could drink from her straw and both be independent of each other. Similarly, if the computer had two network cards, which it does, then I could send or limit all the Cisco Anyconnect connections through one network card while the other network card could send and receive all local access stuff. Too much imagination, or is this possible with pfSense?