If you are going to haul out for the cutlass bearing replacement you should also look at the inside of the boat by the prop shaft.
Many older boats use a 'shaft log' and 'stuffing box' to round out the inside portion of the prop shaft entry. If your boat still has a stuffing box on it I'd recommend changing the packing when you pull out for the other work. Here is one of the best how-to websites on stuffingboxes: Re-Packing A Traditional Stuffing Box Photo Gallery by Compass Marine at pbase.com
If you have the PSS shaft seal I can't help you.