I struck my first tool in 1951 along with my first go around with a swivel knife. To be honest I guess I've learned every minute of those 64 years and I'm still learning. I did glean a bunch of knowledge out of Al Stohman's various books, like "Belts Galore", "How to Carve Leather" (Featuring the ABC's of figure carving and The Dye Chart Method), "Craftool Tech Tips" (really a good source of information), "How to Make Holsters", "The Art of Making Leather Cases" ( vols. 1,2, and 3) and others, all of which have wonderful illustrations and step by step instructions on stamping and carving and the techniques involved. I used to refer to one or the other of them almost daily, but now I've just about got them memorized. Oh, I have to give a good bit of credit to the "Doodle Pages" that Tandy put out every couple of weeks years ago. I have pretty good collection of those too. I think Tandy/LF is offering the collection as a whole for some ungodly price, but it's probably worth it. They were free for the taking back then, one at a time as they were produced. The point is, "self taught' WITH BOOK HELP is probably as good as it gets and allows you to develop your own personal style.
Back when I started there weren't too awful many "Big Names" and you had to kind of learn on your own, unless you had access to someone in a Saddle or Boot shop. I finally had that opportunity about 20 years ago now when I got to spend a year in the shop with my good friend, and Master Boot and Saddle maker, Don Atkinson. He took my rather sizable pool of attained knowledge and added to it and then refined it, and I wound up like I am today
.but I'm still learning. Don taught me, for instance the MOST VALUABLE lesson, that I use every day. The importance of a paper pattern before you even think of cutting the leather, and that you can make ANYTHING you want to IF you can and will make a paper pattern first.
Well, I started off to give you a quick answer and wrote an epistle, sorry. I hope I've answered at least one of your questions.
Paul