Ouch Matt! I hope you get better fast.
A couple of thoughts after reading your post: Cindy is the one who works the winch as I go up and down the mast. She is careful to tie off the line tail to two separate cleats as I go up. So, if the rope does slip out of the winch clutch, the cleat will stop me from falling all the way down. Should it fail while she is adjusting the line tail on one cleat, I am always tied to another. On the way down she reverses the procedure allow only so much free line to move me about 10 feet at a time. Also, at the first opportunity, I will snap on a safety line either around the mast or onto a shroud, I use the MOB harness tether for this.
We use headsets to communicate.
With best regards,
Sailing Vessel - Cream Puff - SM2K - #275
Currently cruising - Tahiti, French Polynesia