GOT IT! You see above, where i wrote:
"But we know i have a legit context, as I draw to it!"
Turns out I didn't. Let me explain.
In my program, I have TWO OpenGL views. Running on TWO OpenGL contexts. Which i must switch between using WGLMakeCurrent(), in order to make them both flush, swapbuffers individually.
The OpenGL view i refer to in this question, is the first to be made current. It has the first texture bound and then it is drawn. At this point the second OGL view is made current, has some stuff happen to it (not important), and then is drawn.
So when I attempt to load and bind a second texture to my first openGL view, I've pulled the "old switcheroo" on myself and am trying to bind it to my second view's context (because it is current at this point). Which explains why the first context still had the old pixel data in it. As I'd technically never called glDeletetextures on it
A quick call to wglMakeCurrent(handleInHere, parentwindowhere), before myTex->reloadTexture("filename") call, and my textures are loading and replacing themselves at my beckoned call.
Thanks for your previous help guys.