A sterndrive needs three holes through the transom, at or below the waterline: one for the drive shaft, one for the shift cable and one for the exhaust. BoatUS points out that the only thing keeping the sea out of all three is the rubber bellows, clamped where they're hard to see. After hurricanes, it says, bellows failures are the second biggest cause of boats sinking at the dock.
How a surveyor checks it
All three bellows. With the boat out of the water, the drive has to be moved port, starboard, up and down to see as much of each bellows as possible. BoatUS's list: cracking, rubber becoming brittle, rust showing on the bellows, and corrosion on the stainless clamps.
Marine growth. Barnacles and broken shells can be razor sharp and slice the bellows. Any growth has to go.
Inside the boat. Water tracks at the transom pass-throughs and standing water in the bilge. A bilge pump that cycles at the berth is a reason to look at the bellows, BoatUS notes.
The age. Every drive maker has a replacement schedule. BoatUS notes most agree a 5-year-old bellows is living on borrowed time.
The rest of the drive. While you're there: the prop for fishing line, which can damage the oil seals, and the drive oil. BoatUS says milky white oil means water has got into the drive.
What decides the grade
Any split, or water tracking in, is an A: the boat shouldn't be left afloat. Old, brittle or unrecorded bellows are a B. Sound bellows with no date are a C.