@jhn11, there are a few things you can do here to render correctly. There are two threads that can help you with this. The first is one that dealt directly with a drinking glass where one of the best solutions was to split the inner faces from the exterior faces which allows you to make use of backface culling to manage some of the sorting issues.
Another thing that can help you is to handle the decal on the glass in the shader instead of with another mesh. There was a thread about this question in applying a decal to a skateboard deck so that you can see the wood grain beneath a decal that can be swapped on the fly.
Another example of something like this is the soda bottle demo we created for the last release which also uses a label on glass. In this example, the label uses alpha and transmission values from texture to create the opacity for the label separate from the refraction of the glass.
Let me know if you have any questions about any of these methods, but I think a combination of these examples should get you rolling in the right direction.