Doubled Die Vs Machine Doubled And Other Questions

Hello all, I inherited a small coin collection that doesn't seem to stick to any certain type of coins.

My uncle just has a bit of everything (well I'm sure not everything it just seems like a decent spread to my newbie eyes). Some stuff is graded and most isn't. Since receiving it it has sparked my interest and I have added a few things I thought were cool while looking into coins and learning a few things.

One thing I'm really struggling to understand is the doubled die vs machine doubled. I've been trying to read up, listen to opinions and watch videos. It seems like there's plenty of people out there that don't quite understand it as well and some who don't understand it that will give their opinions and I find their opinions to be way off base.

I purchased a coin microscope and have begun looking at coinage at a closer view. I'd like to understand this topic better. I've always had a way of being able to explain things to people so they can comprehend things better (a teaching ability for lack of a better term). But in order for one to teach they have to fully understand what it is they are attempting to explain.

So are there any key factors that happen with a true doubled die that don't take place with Machine Doubling? And vice vs? What should I know about the individual characteristics and how they differ from one another?

Also I posted in this thread because I have an example I'd like to post pictures of and see if anyone is willing to look at these pictures and help me understand better which is taking place and why?

I'm still very new not only to coins but to technology too so please if I make a mistake correct me so I may learn the proper etiquette and format in which things are done correctly. Thank you in advance and I'm excited to learn more about your world!