I was able to get it to work by changing the angle of the label's lead line. The behavior is still very strange however because only some of the label's that I adjusted translated to proper rendering. There were some that I adjusted that still did not render.
I also tried adjusting the dpi of my export, that did not help.
I also tried copy and pasting an anno that rendered properly the first time around and replacing a bad one. However when I exported it, the replaced anno was still not rendering properly.
The rendering issue is also impacting two other layer files, both are polygon feature classes. For one of the polygon FC's (parcel boundaries), there are entire areas where the lines are not rendering. In the other FC (city boundaries), all of the lines are rending, but the styling is not rendering properly in one section, it is supposed to be a dotted red line with a white solid background but only the white background shows up.
I will now attempt to experiment with styling and transparency and report my findings.