I think the primary topic to master in C is pointers. This is where most falter. It takes a few years to "master" (if we ever do). Here I would recommend "Understanding and Using C Pointers", Richard Reese. [2]
If you are interested in networking, any of the classic "TCP/IP Illustrated Vols I/II/III", W. Richard Stevens, [3] contain a ton of C code to implement components of TCP/IP.
If you are interested in Graphics, then "Graphics Gems", Andrew Glassner [4] is a good source.
"An Introduction to GCC", Brian Gough, [5] to understand the tooling and its various bells and whistles.
My learning swimming by jumping into the deep end of the pool experience was realized by learning Windows Programming using the Charles Petzold book and navigating through Microsoft Foundation Classes in the late 80s/early 90s. The state of the art in tooling wasn't that great in those days and I spent months with the book to get things going. This was done after I had built a foundation with K&R and a decent amount of Unix network programming.
I see a lot of the other posts recommend more modern books. But you still need to build your foundation on C and Pointers in particular.
Good luck on your journey.
[1] https://www.amazon.com/Programming-Language-2nd-Brian-Kernig...
[2] https://www.amazon.com/Understanding-Using-Pointers-Techniqu...
[3] https://www.amazon.com/TCP-Illustrated-Protocols-Addison-Wes...
[4] https://www.amazon.com/Graphics-Gems-Andrew-S-Glassner/dp/01...
[5] https://www.amazon.com/Introduction-GCC-GNU-Compilers/dp/095...
https://www.amazon.com/TCP-Illustrated-Protocols-Addison-Wes...
For OS, I would recommend looking at Bach (on the design of UNIX) and Tannenbaum's books.
TCP/IP Illustrated, Volume 1: The Protocols http://www.amazon.com/TCP-Illustrated-Volume-Addison-Wesley-...
TCP/IP Illustrated, Volume 2: The Implementation http://www.amazon.com/TCP-IP-Illustrated-Implementation-Vol/...
TCP/IP Illustrated, Volume 3: TCP for Transactions, HTTP, NNTP, and the UNIX Domain Protocols http://www.amazon.com/TCP-Illustrated-Vol-Transactions-Proto...
While they start at much lower level than generic patterns, they build the basis to understand the core of networking, and the the later books go into details about effective usage of the protocols.
In no particular order:
1- http://www.amazon.com/C-Programming-Language-2nd-Edition/dp/...
2- http://www.amazon.com/The-Answer-Book-Solutions-Programming/...
3- http://www.amazon.com/The-Standard-Library-P-J-Plauger/dp/01...
4- http://www.amazon.com/C-Traps-Pitfalls-Andrew-Koenig/dp/0201...
5- http://www.amazon.com/Expert-Programming-Peter-van-Linden/dp...
6- http://www.amazon.com/Data-Structures-In-Noel-Kalicharan/dp/...
7- http://www.amazon.com/Data-Structures-Using-Aaron-Tenenbaum/...
8- http://www.amazon.com/Mastering-Algorithms-C-Kyle-Loudon/dp/...
9- http://www.amazon.com/Code-Complete-Practical-Handbook-Const...
10- http://www.amazon.com/Design-Patterns-Elements-Reusable-Obje...
11- http://www.amazon.com/The-Mythical-Man-Month-Engineering-Ann...
12- http://www.amazon.com/The-Programming-Language-4th-Edition/d...
13- http://www.amazon.com/The-Standard-Library-Tutorial-Referenc...
14- http://www.amazon.com/API-Design-C-Martin-Reddy/dp/012385003...
15- http://www.amazon.com/The-Linux-Programming-Interface-Handbo...
16- http://www.amazon.com/Computer-Systems-Programmers-Perspecti...
17- http://www.amazon.com/System-Programming-Unix-Adam-Hoover/dp...
18- http://www.amazon.com/Memory-Programming-Concept-Frantisek-F...
19- http://www.amazon.com/Memory-Management-Implementations-Prog...
20- http://www.amazon.com/UNIX-Filesystems-Evolution-Design-Impl...
21- http://www.amazon.com/PCI-System-Architecture-4th-Edition/dp...
22- http://www.amazon.com/Universal-Serial-System-Architecture-E...
23- http://www.amazon.com/Introduction-PCI-Express-Hardware-Deve...
24- http://www.amazon.com/Serial-Storage-Architecture-Applicatio...
25- http://www.amazon.com/SATA-Storage-Technology-Serial-ATA/dp/...
26- http://www.amazon.com/Beyond-BIOS-Developing-Extensible-Inte...
27- http://www.amazon.com/Professional-Assembly-Language-Program...
28- http://www.amazon.com/Linux-Kernel-Development-3rd-Edition/d...
29- http://www.amazon.com/Version-Control-Git-collaborative-deve...
30- http://www.amazon.com/Embedded-Software-Primer-David-Simon/d...
31- http://www.amazon.com/Programming-Embedded-Systems-C/dp/1565...
32- http://www.amazon.com/Making-Embedded-Systems-Patterns-Softw...
33- http://www.amazon.com/Operating-System-Concepts-Abraham-Silb...
34- http://www.amazon.com/Performance-Preemptive-Multitasking-Mi...
35- http://www.amazon.com/Design-Operating-System-Prentice-Hall-...
36- http://www.amazon.com/Unix-Network-Programming-Sockets-Netwo...
37- http://www.amazon.com/TCP-Illustrated-Volume-Addison-Wesley-...
38- http://www.amazon.com/TCP-IP-Illustrated-Vol-Implementation/...
39- http://www.amazon.com/TCP-Illustrated-Vol-Transactions-Proto...
40- http://www.amazon.com/User-Interface-Design-Programmers-Spol...
41- http://www.amazon.com/Designing-Interfaces-Jenifer-Tidwell/d...
42- http://www.amazon.com/Designing-Interfaces-Jenifer-Tidwell/d...
43- http://www.amazon.com/Programming-POSIX-Threads-David-Butenh...
44- http://www.intel.com/p/en_US/embedded/hwsw/software/hd-gma#d...
45- http://www.intel.com/content/www/us/en/processors/architectu...
46- http://www.intel.com/p/en_US/embedded/hwsw/hardware/core-b75...
47- http://www.hdmi.org/index.aspx
48- http://en.wikipedia.org/wiki/Digital_Visual_Interface
49- http://www.amazon.com/Essential-Device-Drivers-Sreekrishnan-...
50- http://www.amazon.com/Making-Embedded-Systems-Patterns-Softw...
51- http://www.amazon.com/Python-Programming-Introduction-Comput...
52- http://www.amazon.com/Practical-System-Design-Dominic-Giampa...
53- http://www.amazon.com/File-Systems-Structures-Thomas-Harbron...
54- ...well, I'll stop here.
Of course, the equivalent knowledge can be obtained by trial-and-error, which would take longer and might result in costly errors and imperfect design. The greater danger here is that a sole developer, without the feedback and interaction of even a small group of capable and experienced programmers could simply burn a lot of time repeating the mistakes made by those who have already trenched that territory.
If the goal is to write a small RTOS on a small but nicely-featured microcontroller, then the C books and the uC/OS book might be a good shove in the right direction. Things start getting complicated if you need to write such things as a full USB stack, PCIe subsystem, graphics drivers, etc.
http://www.amazon.com/TCP-Illustrated-Protocols-Addison-Wesl...
(Didn't even realize it had been updated until I checked!)
Personally, I think if you understand the fundamentals, you will quickly realize things like software defined networks and CDN technologies are just abstractions on top of other stuff.
[1] - https://www.amazon.com/TCP-Illustrated-Protocols-Addison-Wes...
[2] - https://nostarch.com/tcpip.htm