I think it is worthwhile to first look into the fields of Complexity Science/Complex Systems Science and Systems Thinking/Systems Theory for overarching insight

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 https://en.wikipedia.org/wiki/Complex_system and https://complexityexplained.github.io/ https://complexityexplained.github.io/ ] and [ https://en.wikipedia.org/wiki/Systems_thinking https://en.wikipedia.org/wiki/Systems_thinking and https://thesystemsthinker.com/systems-thinking-what-why-when-where-and-how/ 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 https://aosabook.org/en/index.html