But if you are like me, and it sounds like you are.. i would still do it.
It's interesting when you start poking at the boat like this actually.. my cutlass actually needed replacement, which lead into an avalanche of repair and replace last winter. i went in to replace the cutlass and really only the cutlass.. what turned out being replaced was..
Cutlass - too much wiggle
Shaft - couldnt remove without dropping the rudder and it was scored.. so cut it to remove.
Coupling - rusted beyond reuse
Prop tuned - why not, it was off already
Transmission rebuild - removed and inspected since the shaft was out and discovered output shaft splines were trashed
new damper plate - always replace when you have the transmission out
Engine Mounts - noticed during realigning the shaft that the engine mounts had dropped.
New oil pan - while i had the engine up in the air the amount of rust around the oil plug was horrible and i poked a hole in it easily.
New fuel lines - moving the engine exposed cracks in the fuel lines
New coolant lines - moving the engine around exposed cracks
New exhaust hose to the muffler - moving the engine exposed cracks
new fuel tank - found diesel in the bilge while aligning the engine
new hot water tank - when replacing the fuel tank i noticed the hot water tank was rusted and leaking
So if it aint broke dont fix it? But at 27 years, it might be time to start pealing things back a little for some major inspection. I'm not the guy that lets stuff break to fix it..