The shaft can get 'necked'ie where the packing is agroove will form.adjustment causes the packing to compres in the groove, when in gear the prop thrust moves the shaft forward and friction=heat occurs, this will also harden the packing. if the shaft has awear groove then the gland will never work.Unsrew the nut and pull it fwd to expose the shaft where the packing runs. You got a groove right? A pro(cest moi) can fix it by minimally installing a one piece rubber seal- swedish starts with v- the seal part will be on unworn part of shaft.the pro may need to go as far as replacing shaft, ,coupling skeg bearing flex coupling bolts re allighnment etc.its a boat job right? Some early catalinas were fitted with bronze shafts-softer than stainless.If there is an experienced marine mech who has done lots of shaftline work in your area why not consult him for an appraisal? the whole system needs to be assessed as to easiest best result.Cheers
harden the packing
I think Sonofason may have come the closest to putting his finger on the problem when he identified the possibility of shaft damage. If that's the case, the best material and installation practice won't count one whit. New undersized packing, new oversized packing, new oversized packing which has been hammered back to the correct size, shouldn't cause this many problems.
Again, as I mentioned in post #36, removing the nut is quite simple and temporarily sealing it (using string) is just as easy. Then you can assess the condition of the shaft, packing, etc. And,
more importantly, you can report back to us just what is going on in there. I don't know about the rest of you, but this one is giving me sleepless nights wondering

WHY

.