First off, I know the true answer to my question, go to your shop and get another fit, but wanted to pose the question anyway.

I've noticed my left leg is smaller than my dominant right, probably most have this situation but been doing some trainer rides and doing some single leg exercises and now noticing that the fluidity on my left leg has a dead spot. It happens right as I'm coming over moving forward (~10:00 position relative to the non-drive side). I noticed two things as well, I feel almost my left hip tightens as it nears this pedal position and also if I watch my knee, it doesn't track straight but moves in the so-called "figure eight" motion.
My right leg does not have these issues, as I can fluidly pedal and to me, it looks like my leg moves fairly up and down with very little lateral tracking.

Does it sound like I need either the cleat wedges/spacer or maybe the Specialized BG inserts to correct both a potential leg length issue as well as foot position?

unless you have had a medical/pt diagnosis of functional or skeletal leg length discrepancy, i'd stay away from trying to "correct" your symptoms along those lines. by introducing one or more new variables into the system, you are more than likely going to find it hard to get clear results.

by looking at how one leg tracks when doing single leg drills, you are including a lot of other body mechanics (i.e. the things the rest of your body does to compensate for only using one leg). So your body is more coordinated at doing one-legged drills on one particular side, not surprising. We all have a dominant side.

the more pertinent question to me is, how do your knees track when you are not doing single leg drills? if they track well, i'd say just work on your coordination more via the single leg drills, and see if they don't even out.

I'll clarify that then, even during normal two-legged pedaling, the left knee wobbles. The main thing I notice when doing the single left leg is almost less flexibility in my left hip as my foot reaches ~10:00.

i'd give you my advice, but it is well summed up in this thread:
viewtopic.php?f=8&t=80853

good luck and let us know what helps!