Cutlass bearing or something else?

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Yes, try rotating the shaft by hand while you and your friend have the stuffing out of the box. Don't worry about all that water coming in. :) It did not squawk, but I once had a misaligned shaft strut due to prop entanglement with a mooring line, and that made the shaft impossible to turn by hand. I ran with it for about ten months before hauling and having it re-targeted and new cutless bearings in all four struts.
 
Thanks guys. I had the wife put the boat in gear at the dock while I listened/watched in the engine room. A little clunkier going into gear than I expected, but I’ve never listened to shifting in the engine room before. There was no shaft noise, and I couldn’t see any movement in the shaft. After shutting down, I pulled the gland right out of the stuffing box. About the same effort as before to turn the shaft with my small strap wrench. I was able to turn the shaft by hand using both hands (1 3/4 shaft).The transmission fluid is as clear as glass, no particles or dust in it. Next step is to take the boat back out with a buddy so one of us can observe the transmission/shaft in operation.
 
prop sing

had the same noise on my mainship, drove me nuts . a friend explained what prop sing was, changed the wheel and noise went away, but everything was lined up perfect, could spin shaft from inside with no problem. if your shaft is tight ,& moving up and down , check alignment. or could be spun cutlass Bering either way something happened.may have hit something .
 
Took the boat out today with a buddy. Ran up and down the harbor, fast, slow and in between, straight and in circles, forward and reverse. We alternated between the helm and observing in the engine room. And saw very little. The port stuffing box clearly vibrates, but it’s not extreme. The starboard stuffing box vibrates too, although a little less. There is no perceptible flexing or vibration at the shaft log hose. Both stuffing boxes were cool, adjusted one to drip a little more, the other a little less. No humming, singing or squawking from the stuffing box, shaft or transmission. We happened across the harbor pumpout boat. We stopped for a pumpout so we could say we accomplished something. Next step is to go back where I was when this started - pack up the Admiral and some baloney sandwiches and head out for a few days. When I get back, I’ll check with my dive service to see if they have a diver/mechanic who can do a knowledgeable assessment of the cutlass bearings in the water. Thanks for all the suggestions. If I eventually find something, I’ll post it here.
 
You mat have already found the something. If there were an issue with the packing, you may have addressed it with all the adjustments on the stuffing box.

Ted
 

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