Yes, that version of RSLogix 5 is very old. I only can go back and find verion 4.1 here which came out June 2000. So your version was probably 1-2 years earlier. Which means it was designed to run on Windows 95. Not at all unusual that it would not run on a modern operating system like Windows 7 or Windows 10.
As suggested, you should use your VM with a serial connection. The PCMCIA cards are not supported by any virtualization package I am aware of. The newest driver Rockwell had was for Windows 2000/XP. I remember using that driver in Windows 7 without any issue. But I never got my PCMK to work in Windows 10. Remember it was designed initially for DOS. Sometimes it would work, but once I disconnected it would stop working. I had to uninstall the Windows driver and reinstall to be able to reconnect.
Or find an old laptop and install Windows 95. Windows 7 32-bit requires RSLogix version 8. Windows XP SP3 requires RSLogix 5 version 7.
OG