It took some time but finally she got it. The problem is the bearing was a little thicker and the clearance to the hull after the coats of paint etc narrowed the space down to < 3/16" from the hull.  Now there's a good 1/4" again.
I always get stressed out when we go to put it back up again. Worrying about it falling on to the concrete and getting damaged, or falling on one of us. It must weigh 250 lbs at least, and it'll be even heavier once it's full of oil, which is her next project.
The photo shows  an anode in place. There's a bit of silicone behind it.

Originally, the bottom bolts (photo left) were going to aim down, but that meant washers would need to be added because of the now reduced height. Somewhere we have heard that washers aren't a good idea for one reason or another so we'd rather not. Gena measured and figured the bolts could be inserted from the bottom flange up before the rudder was on. I was skeptical but hey, it worked! Just.

Now the rudder is happily in place, it can be filled and we won't have to worry about it for a long long time. According to the bearing manufacturer, Thordon, it's the best there is.

I can only silicone the rubber to the floor as the pedestal will need to be removed and flipped down for hauling because of it's height.

The little hole is for the wiring for the horn switch, compass light, and my pedestal display unit.

The center hole is of course for the chain and the shift /throttle cables.
 

I've done my best to keep everything straight so I hope it all goes in without any problems. I tested the cables through the loop, not visible in the photo, and it looks like they'll clear the chain by at least an inch.
Can't wait until she's all in place!