I've been sailing now for a few years and single hand my 30' with confindence in most conditions. I've learned that careful planning and common sense = good luck.
Since I often sail with crew that have limited/no experience I have also learned that even with a crew of four, I'm still single handing.
One thing I have trouble with is the fear of the evil lobster pot bouy. I sail in New England so there are plenty of them out there, even in the deeper waters of Block Island Sound. Some of them are forced two feet under when the currents are running strong.
I've known people to snag them in their prop even when they are NOT motoring. I snagged on in the harness of my dingy one evening, an easy fix once I figured out the problem, but it was dark and it took some time and a bit of stressing to figure out why we slowed to 2 knots.
So, how to avoid them at night without constantly scanning the water with a light? Or just don't worry about them and leave your chances to fate?