Some of us here have designed a lot of things and experience shows that you have to ask a lot of questions to get a feel for how something should be done, before looking at the mechanics of it. Otherwise it's like answering the question ' How do I make a car?' without finding out whether the asker has in mind a Lamborghini or a Nissan Micra.
To me, the most important thing you revealed was this:
I have considerable experience of retractable cable mechanisms in commercial use. They get KNACKERED!! Not just in public areas but in upscale offices and conference rooms. The high-end commercial units sell for upwards of £200 each and some last a year before they are pulled to pieces, springs broken, rollers jammed, connectors squashed and fatigue failures in the conductors. I have personally lain on my back in the middle of the night under boardroom tables fixing and changing them.
So, my advice to you, before trying to find a detailed solution, is to define as well as you can, what you want to achieve. How many mating cycles? How many retraction cycles? What maximum pullout force? Ballpark price? Then if you ask for help, communicate all of this in the enquiry, so that people can get a handle on what is needed.