I have followed this topic with curiosity and see that you have done a good job in cleaning up the machine. A will send a few comments which may help. Looking at the pictures from the front, it looks like the wheel is quite thick. The Fleming Gray wheels from this vintage machine should be 6" diameter x 1/4" thick x 3/4" arbor hole. If your wheel is thicker, you will get an off center dress. Fleming Gray does sell several wheels of this size. https://fleminggrayskatesharpeners.com
Trying to get the hollow setting may be tricky, but it can be measured. Use a ruler or something similar to make a straight line along the center of the pivot point on the arm dresser to the front of the diamond dresser. (You probably will want to do this with the wheel cover removed.) The distance from the line to the tip of the diamond will be the ROH. If that is measured accurately, you can then mark the dresser for the various hollows.
The skate clamp is critical to getting good results and must be properly adjusted to the right height for even edges. The holder that I saw at the beginning has a very old ramp style adjustment, which is hard to set up accurately and make minor adjustments. You might consider updating this to a newer/better type.