Greetings Fellow Top Hatter,

Good to see you are putting on 4 coats of anti-foul, remember it will be a minimum of three years before you have to slip again to redo.
The SS rudder bolts, I actually use threaded rod with locking nuts, will only need to be replaced if they are showing signs of pitting.
I carry an extra three as they are easy to replace if needed, which I've only done once in the last 10 years.
Annodes should need replacing about every three years on a Top Hat, but sooner if showing signs of reduction.
Prop speeds requires 2,000 plus revs and speeds over 10 knots to work.
I've tried it a couple of times on Seaka with poor results so not worth the money.
A plastic bag over the prop for those long periods of non use is a better option.
If the ball valves are tight, or firm to use, they should be good.
If your'e a Mk 2 or 3 you should check for osmosis after you have wet sanded the existing anti-foul.
They show up as shallow domes from 20 cent size and up.
Now the cutlass bearing.
If your shaft comes out directly to the rudder [ie not out to the side of the rudder] you will have to remove the rudder.
This is easy if you are lifted out and drop the rudder before they put you down, but if not you will require 800 mm clearance below the keel and horizontal room to drop the rudder out to allow removal of the shaft. Length of the new cutlass bearing should be 150 mm and if it doesn't fit the tube it will need to be turned down in a lath so as to remain truly in line with your motor. Fix in place with industrial grade Araldite.
What I'm really saying if its working and you have no thumping of the prop shaft and its not loose as per Gary's comments, leave it alone!
Enjoy your time at the slip

as I know its a dawn to dusk task