Thank you for the response... After glancing at a few pages describing liquid columns, and realizing each of them seemed to require a thesis and full evaluation on how they work, I figured I'd take one more look at my CSS to see if there was a simpler solution.
What I ended up doing was:
1. Taking a print screen of my current layout
2. Pasting into Adobe Fireworks
3. Measuring the distance from the top of my sidebar, down to the footer (in pixels)
4. Found the "container" in my CSS code, and changed the height to match the pixel measurement from step 3.
EDIT:
Turns out that setting the container to that measurement locks the footer to that height, even if the pages are longer... attempting to fix that now.