[rramadass]

I think it is worthwhile to first look into the fields of Complexity Science/Complex Systems Science and Systems Thinking/Systems Theory for overarching insights : [ https://en.wikipedia.org/wiki/Complex_system and https://complexityexplained.github.io/ ] and [ https://en.wikipedia.org/wiki/Systems_thinking and https://thesystemsthinker.com/systems-thinking-what-why-when... ]

For Software specific issues i highly recommend David Parnas' collected papers in the book Software Fundamentals. He and his colleagues defined much of what is mainstream in today's Software Architecture/Organization practice.

Finally, the case studies given here are a great source of insights: https://aosabook.org/en/index.html

[kqr]

Am I doing something wrong if I'm unable to find that Parnas collection as a digital book? I've read some of his papers and they were very influential on me. Would love the book but I rarely have the energy to bring a print copy of books.

[rramadass]

In this case the "paper copy" of the book is very much worth it :-) The articles are all foundational, timeless and gets to the heart of the matter unlike most books today.