The subject is the Space Shuttle and you ask for a reference about
how it unfolded chronologically,
how the decision was made to develop it
what were the constraints and limitations,
what were the technical challenges and how they were solved,
what was tried but didn't work out,
As suggested in comments by myself and Russell Borogove, "The Space Shuttle Decision" aka History of the Space Shuttle Volume 1 by Heppenheimer is an excellent book and available as a free download from NASA at the link. However, the shuttle doesn't make an appearance until Chapter 3 and the book focuses heavily on politics. This book addresses a lot of your parts 1, 2, and 3, and some of the others.
For the more technical parts 4 and 5 I suggest another book by the same author "The Development of the Space Shuttle" a.ka. aka History of the Space Shuttle Volume 2 While still covering politics, this volume is much more technically oriented with chapters dedicated to each of the major subsystems such as the main engine, the other propulsion systems, thermal protection, software and avionics, etc. Personally I prefer this volume, and it covers the rest of your question. Unfortunately, I have not found this volume online for free.
Another excellent book that plows the same ground is Dennis Jenkins' "The Space Shuttle" which has been issued in continuously updated editions with slightly different titles for decades. The 2001 version "Space Shuttle - the History of the National Space Transportation - the first 100 Missions" is available for checkout at the Internet Archive.
Again covering much of the same material, less technical than either but eminently readable is "The Voyages of Columbia, the First True Spaceship" by Richard Lewis. Also available for checkout at the Internet Archive.
Finally if you really want the nitty-gritty technical details, I can suggest nothing finer that the two-volume proceedings of "Space Shuttle Technical Conference", NASA CP 2342, available as two large but free downloads from NASA NTRS. (Part 1, Part 2) In June 1983 after the sadly premature declaration of the shuttle's operational status, "NASA organized a technical conference focusing on the design and development phase of the Space Shuttle Program" and in many cases, the actual subsystem managers presented the evolution of their subsystem's design.