BYM:
I don’t see how learning Gemarah will help you (although I don’t discourage it). Your issue seems to be that your entire life’s learning has been on a 5th grade level, even when you went to high school, seminary and beyond. Learning Gemorah on a 5th grade level will not help you understand “the Judaism stuff”. IMHO, you need some heavy Hashkafa (which unfortunately no one really writes in this day and age. “Popular frum hashkafa” is IMHO mostly shallow). I would suggest the Rishonim and Geonim, their Hashkafic works, and looking at them with a critical eye. Then work out for yourself a blend of what works for you. For example, the Chovos HaLevavos is a wonderful sefer, but I can’t agree with his thoughts on predestination, so I personally reject that.
Learning Abaye and Rava arguing about Yeush, although a wonderful thing, will not answer any of your questions.
Hatzlacha.