I implemented some of the more popular design patterns using more real life like examples. You might find them useful :

https://shirazian.wordpress.com/2016/04/11/design-patterns-i...

I'd say when I was first learning about many of the design patterns, this was my biggest hurdle as well. The examples and analogies were unrelated to real-world scenarios and didn't do much to help me understand the concepts.

It wasn't until I came up with my own real-world examples that were specific to my domain and really applied the design patterns in practice that I really started to understand everything. I don't think it's really the real-world example that helped so much as the actual process it took to arrive at an implementation.

Grady booch was working on a "handbook of software architecture". What he was doing is go to companies and look at how systems have been built.

there's a presentation https://pdfs.semanticscholar.org/242a/61777fd7f0f7ded8d9326e...

He was looking at the structure, and the patterns in real world systems

Disclaimer: I haven't looked at it in many years, but I seem to recall Fowler's Enterprise Patterns[1], while covering a higher layer of abstraction, grounded in real world problems.

[1] https://www.martinfowler.com/articles/enterprisePatterns.htm...