I'm getting the feeling wired is the way to go.
How are you attaching the CAT cable to the snake? Wrapping it around the snake (i.e. twisted pair), or keeping it straight using something like velcro straps every 5' to secure?
Scotch 88 vinyl tape about 4ft apart. We end up re-taping all our looms every couple of years as part of our winter maintenance program.
The application I mentioned earlier has had at least 5 years of setups and take downs, all by stage hands. Even though I have a couple of cracks in the outer jacket (I can see the twisted pairs) it still functions for 18 amps and processors on the network. It's being replaced by Rapco DuraCat at some point soon because it wont work forever. For the <$50 we have invested it's been perfect so far.
The trick to saving time as a one-person operating is *packaging* your gear so you can safely handle either the weight or bulk, and keeping things used together, together in the packaging. My current back pain is testimony that I didn't do that right 35 years ago...