Hi Jeremy
One of the key parts is that you have to know 100% which serial port the radio is connected to. Chirp is not able to figure this out on it own. It has to 100% be sure that if the radio is on the USB RS232 adapter that is labeled as Com 14, that you use that port and that port only. Otherwise, you will get the failure you are seeing.
Assuming you are using Windows, can you see Port 14 in Control Panel? If it isn't there, then Chirp won't be able to see it either.
I would recommend that you watch control panel while plugging in and removing the USB adapter you are trying to use. This way you can confirm 100% that it is com 14. It should come and go from control panel.
Don't bother testing with Com 3, 4 or any other port if that isn't the one the radio is connected to.
Do you have another computer you can test with?
I hope that helps.
Mike