Honestly, the best set of docs I read were the design documents (about 30 .doc files) released as part of the Windows Research Kernel, which, uh, you may be able to find if you do some creative googling ;-)

From those I was able to appreciate a lot of the why between the object model, I/O request packets (IRPs), handles, asynchronous procedure calls (APCs), memory section objects... basically all the individual concepts that have no equivalent in UNIX.

....and once you understand those primitives, you can start to appreciate the layered driver model, new thread pool stuff in Vista+, registered I/O in Windows 8+, etc.

Books... my recommendation... Windows Internals is the best place to start: http://www.amazon.com/Windows-Internals-Part-Developer-Refer...

Oh, and basically any article Russinovich has written, check out the list on the articles section on his wiki page: http://en.wikipedia.org/wiki/Mark_Russinovich

(E.g. http://windowsitpro.com/systems-management/nt-vsunix-one-sub...)

Also... my interest in all of this stuff has grown exponentially since I started seeing real world results from PyParallel: https://speakerdeck.com/trent/pyparallel-pycon-2015-language...

The original author was Mark E. Russinovich from "Sysinternals fame", nowadays other developers continue the new editions.

http://www.amazon.com/Windows-Internals-Edition-Developer-Re...

http://www.amazon.com/Windows-Internals-Edition-Developer-Re...

Additionally the books for user mode programming from Jeffrey Richter and Charles Petzold tend to be quite good and full of valuable information as well.