You do know if you aren't careful you'll put an eye out right?
Here is how I think it should go. First, the bearings go into the frame head tube, where they are on picture number two. Then a bearing nut threads onto the outside of the steering stem, this gets torqued lightly to preload the bearing. A second bearing lock nut goes on top of that and gets torqued real tight (so you don't put your eye out).
The upper triple clamp/plate then goes on top of that. Hopefully the top of the forks and the top of the bearing lock nut are level
Kind of like this.
The fact that it is an Earles doesn't really change how the steering stem works.
What I don't understand from you milling and cutting theory is how do you handle the bearing preload seperately from the clamping pressue to keep the upper fork brace on? The bearing preload MIGHT be 5 foot pounds and the clamp nut is 40 foot pounds?
Seriously, leave the bearing in the frame neck. Bolt it up with locknuts then figure out how to mount the upper plate. The upper plate doesn't take all that much stress. Look at the wimpy one BMW used forever.