Hey Mitch. Did you ever get to the bottom of this? I’m experiencing a similar problem with a similar set-up. Premiere Pro CS6 on a MacBook Pro retina. I use a T-Tap to run a signal to a LCD client monitor. The first thing I noticed is that the audio out of my mac (wanting to run it through a little board) is a couple hundred milliseconds ahead of the video from the T-Tap. No problem. I picked up a little delay unit to compensate.
Even still, over time the video starts to fall behind. I suspect it’s not the delay unit because it’s staying in sync with my Program window. Only the LCD drifts behind. A double-tap of the space bar obviously fixes it. but that’s no solution.