I have actually done this job on a C28 and wrote it up here about 6 years back.
Not sure if Geoff can search the forum with my user name?
Anyway, you have to pull the prop shaft to get the rudder off.
So you may as well do the cutless bearing and check the bit of copper tube that's used as a shaft log in these boats.
It was only 2mm wall tube on my boat and I know there have been cases of corrosion.
Rudder shaft and prop shaft on this C28 were 1 inch but it was the original YSE8.
The hard bit was prising the fibreglass cover off the top bearing. It was just bogged into the cockpit floor when the yacht was built and a lot of bog had to be ground away.
So the order is, or was in my case:-
Remove tiller, lose woodruf key, remove prop, attempt to release shaft coupling to remove prop shaft for about 8 hours. Sheer off set screws in coupling, give up and cut prop shaft in half. Unbolt coupling from motor and remove remains of shaft on workbench with heat. Order new shaft from Porters (only $400 delivered) Remove other half of shaft, then lower rudder gudgeon. Discover rudder is full of water as it drops about 2 ft into rudder pit on slipway.
Check copper rudder tube for corrosion (same as shaft log). drain water from rudder and attempt to bog up.
Reassemble with new rudder bearings, new cutless bearing, new dripless seal, new shaft, replace lower gudgeon mounting bolts, buy new woodruff key.
Wait 4 weeks and then have wife say "I'd like a bigger boat". Sell yacht to the next person safe in the knowledge they will have no issues for the next 25 years because I just did all the engineering!!
Just my experience...
Seriously, if your yacht was repowered in 2005, you may find the cutless bearing is fine, plus the coupling will probably be way easier then the corroded 30 yr old one I had.
The top bearing on my boat was extremely worn. The rudder used to rattle when the boat was at anchor and you could pull it forward by the tiller about an 1/8th of an inch.
The boat was much improved with new rudder bearings with no water over the cockpit floor motoring as Geoff described.
Hope this helps.
Brett