Wobble woes
Altho a new cutless bearing permits no play in the shaft, one might get a bit as the system ages. Folks at my yard say if you get more than about 1/16th-inch slop in the shaft, time for a new cutless. If you wait til it starts thumping or causing vibration, you risk shaft, shaft coupler, transmission damage as well as wobbling out the journal through which your shaft extends out the bottom of the boat. This is big bucks. Here in Texas, it costs about $600-$700 to quick haul the boat, block it for a day, yank the shaft, install a new cutless bearing, reinstall the shaft and splash the boat. You might, since you are going to have it all out anyway, want to spend an extra day and maybe as much as another $100 or so to have a machine shop look at your shaft and retrue it if need be and maybe have the local prop shop clean up and repitch your prop. You will be surprised how much "smoother" your rig will run after doing this.