This afternoon I slathered Icy Hot onto my lower back (didn't really help, but felt good) and went for a ride. We worked on the fore mentioned suggestions (my arms and him not hang on my hands, etc.) and worked on the new suggestions too (transitions, keeping him infront of my leg, etc.). I also opted to drop my stirrups a hole to see if that helped with my legs (slight numbness=lack of grip) and leaning forward, which I think it did (but had it's downfalls too).
It was a very strenuous workout for both of us. Definitely need to work more on our transitions, as he likes to fall onto his forehand and go heavy on the reins, but I kept pushing him forward and we got a few "okay" transitions in (won't said "good" because they were just satisfactory for it being a new exercise for him). While the entire ride FELT LIKE both of us having the urge to fight eachother, we found ways to work it out and by the end of the ride he was definitely moving more forward and he was very soft in his mouth, holding himself up.
Once we improve on these issues, I will get another video for critique. Regardless of the stirrup lenght, after riding for a while, I still have issues with weight in my heels due to my legs being progressively more numb the longer I ride. Very frusterating.