How do you plan?

I'm pretty conservative and always plan to be able to swim out even when I'm towing a 2nd scooter. I've had some wonky things happen with scooters and other mechanical equipment that I just don't trust them enough, especially when it comes to my life. I know not everyone is this conservative. In fact, I've heard some gas plan the same whether they're doing a swim dive or a scooter dive.

So what do you do? And why?