I've been working at this all night, and while I'm certainly closer than I was, I'm still having trouble consistently getting .obj files to maintain their textures when exported as .nif files. I don't really need the textures to stay, but the UV maps are a must, and I can't seem to get from Blender to NifSkope without losing all of them.

Simple answer - you can't. The Niftools import/export tool for Blender is not yet equipped to handle Skyrim nifs.

What you'll need to do is import your .obj, make your changes, add material and textures, do your UV mapping, then export again as an .obj. From there, open a similar nif in Nifskope, highlight the NiTriShape/Strip and import your .obj file over it. I say similar nif because you can't change the collision, so find a nif with collision that will fit the new .obj. You'll need to adjust some of the nif's properties such as the BSLightingShaderProperty (material) and BSTextureShaderSet (textures).

Here's a http://tesalliance.org/forums/index.php?/topic/4634-3d-craftworks-importing-weapons-into-skyrim/ that explains it in more detail (it's for converting weapons but the same steps apply).

Thanks, one last little thing. How do I save a UVMap to be tied to the .OBJ such that when I import it to NifSkope it actually shows up? Or is this automatically accomplished?

It will stay on the .obj file on export.