So I seem to have gotten this issue sorted out. My last batch, which was today, I had a Mash Eff of 81.9% and an overall efficiency of 70.3% which I am STOKED about! I adjusted my thermometer which I'm sure played a role, but I think the biggest factor, and I can say this with pretty scientific certainty because it was the only variable I changed in my last two brews. I started not letting any wort stay in the boil kettle. Originally I had calculated the dead space in the kettle and just let that wort stay in there. My theory is that whilst cooling the wort all of the sugars would drop to the bottom of the kettle. And thus I wouldn't be getting them into my carboy. Now I've started stirring while I rack the beer from the kettle and pouring all of the liquid from the BK into the carboy. Next time, I'm going to try draining the dead space from my mash tun. I don't think this will have much effect since all of the sugar should be in a relatively homogenous mixture in the mash.