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Shotchas said..
So while you have the engine out I recommend you unbolt the engine mount brackets and get them sandblasted and hot dip galvanized. Then I suggest you have an adjustable set of solid engine mounts made up.
They will be pretty much the same as the flexibles you have but minus the rubber and therefore that much shorter. You will then need hard wood or hard plastic blocks to go under them to make up the height.
Solid mounting the engine is the only way you will ever be able to maintain a decent engine to propellor shaft alignment.
While you have the gearbox separated from the engine, drill a drain hole in your bell housing. You could tap it and put a plug in it if you can get at it when the engine is back in. Then you need to check your drive plate for loose springs and rust. Replace if necessary.
The drive plate will have an SAE spline. It will most likely be an automotive clutch plate minus the friction material and a fair bit cheaper than buying a "marine" drive plate.
Also while you have the engine out, remove the sump and set it up with a drain hole at the rear with an elbow and pipe leading to the front of the engine with a stop cock on the end of it and a screw in plug.
Doing this will enable you to do oil changes very easily and drain the sludge from the lowest point of the sump as well.
You might not have the skill or gear to do this yourself so bite the bullet and pay to have it done professionally.
What you refer to as the "Cutlass" bearing is not a cutlass bearing. It is the
"Stern" bearing.
Cutlass is a brand name referring to "Cutlass Rubber Bearings" from which I steer well clear of. I much prefer a Tufnol bearing.
Google and Wiki it all up to learn. Look up lignum vitea as well. Then of course you need to make sure you have a good stern gland that is easily serviced as well. It is one of the things that keeps the briny out of your boat.
While you have the donk out get all this stuff right. It will save you a lot of dramas in the future.
Cheers Cisco.