I think the way to go about it is read some books gradually on history of computing & the various designs and rationale that evolved over time. Consider these sources:

1. The Annotated Turing.

2. A History of Modern Computing 3ed

3. The ACM Turing award lectures

4. Theory of computation - Dexter Kozen

5. Coders at Work

6. Hackers: Heroes of the computer revolution

Additionally, you could subscribe to Communications of ACM, which is a computing oriented monthly magazine.