So as you can see, we've got some improvements. After some initial confusion about attempting to use pointers before the objects they pointed to were created (hint: Access violation reading memory at 0x0000....) and confusion about texture changing and world positioning, I implemented a custom font system through textures. As you can see, I also figured out what needed to be done for transparency, but the images are a bit rough around their edges still.
Can't wait until we get a scrolling background in there, it should look great. I also would like to know how the framerate is being capped at 60. I'm not really sure if we're doing that on purpose or not.../shrug...just want to analyze how the performance of this is doing.