You'd normally have an electrical connection set up so water won't pool in it.I am not sure it would help much? My concern is that it might not be waterproof...
I have no issue with a headphone type plug as long as it is sealed, the plug should come apart if the cable snags something rather than ripping the wiring out of something. It will need cleaning but so do the weatherproof plugs on cars and trucks, bike cleaner will help the water get in.