I have been hearing OctoPrint On Air #24...
There is a reliable way of identifying serial ports which I use routinely: in Linux using udev I can assign a name to a serial port based on the adapter's serial number.
I just add a file /etc/udev/rules.d
ATTRS{manufacturer}=="FTDI", ATTRS{serial}=="A6007yX8", KERNEL=="ttyUSB*", MODE="666", SYMLINK+="ttyUSB42"
I believe that there is a method to fix a COM port number manually in Windows too...