A DRO is a huge aid in this, once I got it set up (mainly using an original 25-20SS case as the guide). You can probably get it close with judicious wheel reading.
There is no need for annealing until you start forming the neck.
The forces involved are not all that great - until you get to the last 1/4 or 1/8 inch, it doesn't even register on my force dial.
As far as making it, I saw no difference in what brass I used. Mostly I used new Privi Partizan .223. I also tried it with some old Lake City 5.56mm and it formed up same as the rest. I haven't yet shot it, though. In fact, the one case you see me forming in the press is a used LC.
Yes, I use Imperial Sizing Wax for this and everything reloading.
It is slow and tedious work. I've been working on this bag of 50 for months (intermittently). Lately, I've been on a big push to get it done so I can free up my lathe for other work.
I did find that pressing to a line worked better than trying to press to a particular pressure. To establish the line, I just pressed a bit more at a time until I liked what I had, then I just marked the piston where it was flush with the top of the die.