You are going to need some external device with I/O. I would go with a microcontroller board that with one usb cable you can power and communicate, stm32 discovery I think, mbed, an arduino or avr, etc. Does the pc actually care? you could just have a microcontroller board always be trying the I/O and have a pass and fail led, plug the cable in fail led goes off pass goes on, next...Opens the door to more boards msp430 launchpad, and others. Or just roll your own at oshpark.com or other similar place.
I assume you realize there are off the shelf cable testers that do this and impedance, capacitance, check for shorts, etc. And have various standard connector modules depending on what connectors you are using on each end. With a microcontroller board or a pc you would need to fashion a fixture to put the connectors on anyway.