I lived in WI for 14 years and love the summers there for riding. Yes, the life vest laws are pretty loose which is sometimes nice.
A few years back when riding without a vest wasn't such a big deal, I did a tantrum next to a cop boat with 3 DNR officers in it and all they said was "nice flip" and kept on going.
Most of the time when I surf, I don't wear a vest. Being from Hawaii originally, it just doesn't feel right
I know it's not safe but that's what spotters are for!