Some time ago, a Crealock 34 owner, Dave Pomerantz, posted detailed instructions on how he replaced the cutless bearing on his boat. He did not drop the rudder, but was able to extract the old and install the new bearing with everything in place. As far as I know, the procedure would be identical for a C31.
You might be able to search in the archives to find Dave's post.
On longevity, I'm surprised to hear Steve needs a new bearing already. Maybe ours was replaced at some point by a previous owner (although I found no indication in the maintenance records), but we've never had to replace it.
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Pacific Seacraft Crealock 31 #62
NEVER CALLS CRUISINGDAD BACK....CAN"T TAKE THE ACCENT