As someone who's learning programming right now, do you have any suggestions on how one would go about finding and studying these successes and failures?

First, failures aren’t always obvious, and second, studying them isn’t either. This would likely need to be a formalized course. Still…

If people want to know why Microsoft hated DOS and wanted to kill it with Xenix, then OS/2, then Windows, and then NT it would be vital to know that it only came about as a result of IBM wanting a 16bit source-compatible CP/M which didn’t yet exist. Then, you would likely want to read Dissecting DOS to see what limits were imposed by DOS.

For other stuff, you would start backwards. Take the finished product and ask what the requirements were, then ask what the pain points are, then start digging through the source and flowcharting/mapping it. This part is a must because programs are often too difficult to really grok without some kind of map/chart.

There is likely an entire discipline to be created in this…