Sharps,
You are doing great on this project,your cases look really good. To find the depth of the grooves in the 16ga,slug the barrel to fomd groove dia.,measure bore dia.and subtract it from groove diameter, divide the result by 2. It may not be as accurate, but you should be able to measure directly with the depth function on the caliper in the photo.To answer your question about sizing 44-40 bullets to .415 or a little larger,yes you can. I size 43 Spanish bullets from .439 to .425 to use in lead bullet loads for my .404 Jeffery.This wipes out the grease grooves, so I lube with spray lube or Alox. Since it looks like you will be using Black Powder, Alox won't work for you. You might have enough grease groove left to be useful,especially if .417 bullet fits the neck of a fired case and you decide to use that size.It helps if you lube all grooves, including crimping groove. Lee sizers are pretty cheap, and you can get most any dia.you want.The idea is to size/lube to the closest size your lubrisizer will handle, then final size in the Lee, unless you decide to use "white"powder and Alox will work.In this case skip the lubrisizer.All this goes for 44spec/mag bullets also and one of them may be closer to the weight you want.One of your 40-70 bullets, if soft and used "as cast" might "slug up" enough with BP to be usefull. It's worth a try any way. With cnc machines, you can have custom molds made for a really good price now.
Mike