I still have and use some older moto radios, namely sabers, HT1000's, maxtracs and MCX1000's. I can't recall what vintage the CM300 is, if it's the older 8 bit software you might be out of luck. The first generation RSS ran on 8 bit machines and relied on the hardware clock for I/O timing. Run it on anything but an "XT" or "AT" machine and while the software would work, it couldn't read or write the radio. DOS software eventually became compatible with faster machines (e.g. 386/486) but some was never updated (I think HT600 fits into that category). Point of all this is running the software from a "DOS box" should be pretty straightforward, it's the radio I/O and port mapping that you'll have to work through. My answer? A 35 year old Toshiba 286 that boots from floppy drive. If that ever craps out I'll be in trouble. My approach would be to mess around with a DOS terminal program which offers user control of COM ports. Once you figure out the magic settings of DOS box to allow that to work then that's what you'd try with the RSS (hardware timing notwithstanding).
Mark K5LXP
Albuquerque, NM