[Sabreman]

I've done the job 3 times. Twice on my 28 an once on my current boat. Some things to keep in mind:

1. Any good marina has a hydraulic press that will extract the cutlass bearing without shaft removal. I've seen it done but that is not how I did it (because I'm cheap).
2. You have to determine why there is play. It is a sign of wear - in my experience due to engine misalignment or a bent shaft. Of course, if the bearing has been there a REALLY long time or had a lot of motoring, it will wear.
3. If you pull the shaft, look for scoring where it passes through the cutlass bearing or at the stuffing box. Replace the shaft if there is ANY scoring. If you're doing all this work, replacing the shaft (and engine coupling) is cheap money (~$300). To be honest, it was easier for me to just cut the thing out and install a new shaft.
4. To extract the cutlass bearing, I scored the inside of the brearing with a hacksaw and then cut it away (with a cold chisel) for about 1/3 of it's length. I extracted the whole thing with an extractor made from a 1 1/2" pipe, some washers, and 1/2 threaded rod. PM me if you want to see a photo of the arrangement - it's hard for me to describe, but it WORKS.
5. Store the new cutlass bearing in the freezer overnight and transport to the boat in a cooler. Freezing it will shrink the bearing slightly and make installation easier. Coat with dish detergent and PRESS the bearing into the strut using the bearing extractor that I described earlier. DO NOT pound on it. Use SS set screws and threadlock after GENLTY drilling a VERY shallow detent in the new cutlass bearing (once installed). Don't drill through the thing.

It isn't a really hard job, took me about 4-5 hours. At the same time, I also replaced the stuffing box with a PSS shaft seal. Again, it's cheap money (~$250) and it eliminates a wear point in the drive train. It is also much more forgiving of slight engine misalignment sine there are only two support points - at the engine and at the cutlass bearing several feet away. I have NO play at the bearing after 4 years.