After sanding (thankfully I have a sander), priming and spraying the piece a glossy bright white, I set it up in my room and stepped back to admire. Low and behold, I HATED it. As you can see, the side table already isn't the right height, calling even more attention to it by spraying it the bright white. On top of this, when setting beside the glossy (and adorable) white chair, the room ended up looking unbalanced with all of the white piled into one corner of the space.
Having already spent above my non-existent budget, I needed to find something that would work within my own home. Because the lamp is so tall, I wanted something a little lower than my bed, helping to balance clunkiness of a large bed. I then talked myself into liking the square table vs. a circular one as long as I further complemented the lamp base with additional circular accessories. Finally, with the surrounding pieces all being smooth and the lamp shade being textured, I decided to add more texture by using a rattan cube as a side table to help balance out the two finishes.
After accessorizing the dresser a bit more with an aloe plant potted in a shiny white pot, I was finished. Now all that's left is 1) a solution for what to do with the [boring] hutch (featured here), 2) the purchase of some rugs and new curtains and 3) spray painting a few of my frames to get rid of the some of the red (featured here and here).