Ok, given that you are trying to "learn from the ground up" by learning tired old stuff nobody uses anymore, I'm going to suggest --in the gentlest way possible-- that perhaps the problem is that you're starting from the wrong place.
Beginning from DOS is just going to leave you with a head full of old-think that you're going to have to get beyond at some point... holding yourself back is not the way to get ahead... Especially when you realize the way things have changed... Since Win2000 you have no direct access to the hardware so DOS style graphics programming simply isn't going to work. Beginning with Vista, the "DOS" console window cannot be zoomed to full screen without some serious trickery. Then the final kicker... Windows X64 versions won't even run 16 bit code.
... probably not where you want to be.
You should probably start by
brushing up on C with a couple of console programs then download the
Windows SDK and work on learning the
Windows API and some about
Winsock networking. From there you can move on to graphics coding in
GDI+ and
Open GL and, of course, some
Direct x stuff. You may find OpenGL is attractive because it's multi-platform with implementations for Windows, Linux, Android and Mac.
For the comments about ASM... yes it's handy to know some ASM as there are some situations where it is helpful to "talk with chip" ... However; for most things there is very little advantage in programming whole applications directly in ASM. First; the plain fact is that most of the functions you would be calling from ASM were written in C or C++ anyway. Second; the output of Pelles C (and other compilers) is machine code just like ASM produces, there's no magical "something else" as there is with interpreters like C# or Java.... So long as you're working with a true compiler of reasonable quality (like Pelles) there will be very little --if any-- difference in performance or size between C and ASM.
One of the biggest mistakes computer people make is that they think it's hard... so they go about doing everything the hard way... Reduce your Excedrin bill and just don't go there.