A sad setting of sails (or sad setting’ of sails) is a mess, or even an eyesore. It’s something that’s completely messed up. It’s the opposite of Ship Shape.
12 step recovery jargon referring to someone new who talks about how great life is, now that they'resober. Usually meaning that the person is out of touch with reality.
The new guy seems pretty happy for a dude who has no job, no money and no family. He must be on a pink cloud.