Hey Dawg, Sounds like a well earned rest after being wet and cold and pulling a loose anchor with rode up.
Is this a roller furling? How's he going to get it fixed in one day? It has a hole in it. Did the stitching let go? The whole sail sounds suspect to me.
Does he have a storm jib? A method to deploy it ? How many reefs in the main? What kind of condition is the mainsail in ? How does Standing and running rigging look?
I hate messy boats too, and at sea they are dangerous..everything becomes a projectile.
What kind of safety gear is aboard? Life raft? Radios, ( VHF, SSB? ), First aid, Tethers, Harnesses, Jacklines, Epirb? Flares?
Temps are heading toward freezing at night...the ability to stay dry will be paramount. Good luck.