I've been watching and I see plenty of "right thinking" IMHO so far, but I'll add my own to the suggestions.
I'm assuming that the "quill end nut plate" can actually secure the two outer races, the outer spacer and the outer spacer is precisely parallel.
consider using a pair of 7208 ACBs, back to back, in the lower positions. Discard the snap ring. Machine an inner spacer that, when clamped, will set the preload on the ACBs. Machine an appropriate spacer to fit between the upper 7208 inner race and the inner race of the uppermost bearing. Use a 6307 radial bearing in the uppermost position. Use the existing nut to clamp all the inner races.
Regarding the circular groove damage to the spindle bearing shoulder: If you have access to a quality grinder hand, and the price is acceptable, the best repair is to grind to 100% cleanup. The spindle will sit a few thou higher in the quill but I doubt that would be a problem. Another option is to make a washer to cover the damage. I might start with a
thrust bearing washer which is already hard, flat and parallel. The only modification is to reduce the washer's OD as required.
I would use a sealed bearing for the uppermost position (6307). It's a milling machine and I don't want contamination screwing things up.
I would machine (remake?) the quill end nut plate to carry a lip (or felt) seal for obvious reasons.
If the quill is without any unsealed holes, open, grease lubed ACBs should be fine. The quill interior has to be sealed from ingress of anything that could contaminate the open ACBs/grease.
Good luck.