Sorry @Susquatch, I got the milling direction completely a$$ backwards in my reply to your question 3) above.
To conventional mill, the cutter needs to be in the front of the workpiece (to cut the front step the key) when the table is moving right to left; and on the rear (to cut the rear step) when the table goes left to right.
Yes, you do want to feed into the cutting edge - that way the backlash is not a factor as it is taken out.
In machines with substantial backlash, the preference is not to climb mill (feeding in the same direction as the cutting edge is going) because if it grabs and takes up the backlash, the amount of material that needs to be removed at that instant may overpower the cutter and damage it off. Climb milling does tend to leave a better finish though.
No worries, that's exactly how I understood it. This cutter VS part/table stuff is all "relatively" confusing. (Pun intended.) As Einstein would have said, it's all relative..... LOL!
When I first started thinking about milling, I realized that all milling produces chips because the cutter grabs chunks with each tooth pass. In the absence of a chip breaker, lathes cut springs or strings because there is only one tooth that stays constantly engaged at the same depth from start of cut to finish. Spinning part VS spinning tool. In the same way, a lathe pushes almost all cuts which eliminates backlash during the cut.
But a mill is a different beast.
In my simple way of looking at it, I began by forgetting about all that left right stuff. Parts are either pushed into a cutter edge headed in the opposite direction, or yanked along by a cutter edge headed in the same direction. I figured that pushing eliminates the backlash the same way as it does on a lathe.
Hopefully this will all be intuitive for me some day soon.
I just assumed that it works like a lathe. You always want to fight the cutter in order to eliminate the backlash.