On the 1st question: cartridge cases are made with swaging presses in almost the same way jackets are made. I'm not sure how the head is swaged or milled except for the simple rim type, like a .38 Special... it is swaged fabricating the rim, primer cup and hole, and alpha-numerics, probably in a single operation. For all practical purposes this swaging is done on high speed multi-stage automatically operated powered presses. For more complicated heads, such as rebated or belted, perhaps a lathe is needed to finish the case off.
Other items that will add costs to a simple manual swaging operation:
-lead wire and wire cutter or core mold and lead pot, or purchaced cores.
-calipers
-scales
-lubercating material ( for swaging the bullet as well as greasing any all lead bullets)
-jackets
-books on the bullet Swaging art/science.
(( the price level and range on the above is large, especially if you don't already reload.))
