Play int he wheel.
Joe, This following are probably crazy ideas because it sure sounds crazy to me as I type this but I wonder if flipping the wheel around would help. I only mention this due to the limited experience I've had working on a handful of teak wheels and otherwise for both my E31 (I've had a total of four different ones on our boat before being satisfied with the one on there now) and even one for a C36 that I refinished. I'm pretty sure in the range of about 99% to 101% that the mounting screws visible on the hub of your wheel should not be seen. I know that everything's backwards in that regard due to the wheel box design on your boat vs the more conventional pedestal form that I have but am just tossing it out as a possibility that you might try. I just looked at photo images that I have taken over the years of seven different E31's equipped with wheel boxes and only one of them shows those screws facing forward, the rest of them having the screws facing aft. One of my wheels that I worked on had a hub with an undersized 1/2" hole and I had a machine shop enlarge to 3/4" and along with the 1/4" key slot which needed deepening (is deepening a word???). I only mention this because of the familiarity that grew from all the work I've done on so many wheels. I knew which way to reinstall the hub after the machine work was done: screws not seen surrounding the hub nut. Hmmm, here's another thought. Might it be possible to identify the area of slop in either the keyway slot or the bore and then shim accordingly as has already been suggested? To take this to the extreme, I'm sure any competent machine shop could enlarge the slot to accept the next larger woodruff key if that turned out to be the problem area. I hope my ramblings will serve as food for thought and allow you to come up with your own fix, Glyn Judson, E31 hull #55, Marina del Rey, CA