Bearing Housing - End of Life? + a few other Qs

[vb2oc0371]

This is a 2008 Yamaha 25hp 2 stroke ESH

I'm replacing the water pump and drive shaft seals, and anything else I can while I'm in there. I have the following questions:
1. How bad does pitting have to be before the oil/water barrier is compromised?
2. Are there any tips or tricks to inserting the shift rod boot into the bearing housing? It will go in, but it has to be smashed down pretty good to fit. Will grease help or hurt the seal after it's set?
3. Should I apply gasket maker to the lower casing packing (bearing housing gasket)? I've heard yes and no.
4. Apply Loctite to outer rings of drive shaft oil seals prior to installing? again, I've heard yes and no on this? And I've heard a light coating of grease to slide them in.

See pics below...

1. The bearing housing is pitted. After putting new drive shaft oil seals and a gasket, could this part continue to function in it's current condition?:







2. Easy way to install without munging it up?

[rodbolt17]

myself, that bearing housing looks ragged.
if I had to reuse it I would apply a light coat of 3M weatherstrip adhesive to the seal OD.
use perfect seal on the gasket.
use gear lube to assist in pushing down the shift boot.
the shift shaft cannot be inserted if the prop shaft is still in place.

[vb2oc0371]

myself, that bearing housing looks ragged.
if I had to reuse it I would apply a light coat of 3M weatherstrip adhesive to the seal OD.
use perfect seal on the gasket.
use gear lube to assist in pushing down the shift boot.
the shift shaft cannot be inserted if the prop shaft is still in place.

I appreciate the info.

Thanks