@Ryan T : your get up looks really good overall. As you noticed yourself, the roll to elbow can be improved on the ascent and descend. When you watch carefully in slowmo, you see that your shoulder gets unpacked on the roll to elbow side and the elbow on the bell side gets unlocked. The main reason in my opinion is a bit to much rush. Calmness and attention will help.
- You could pay a bit more attention on foot placement of the bent leg. Try to bring the heel as far back as possible and maybe a bit more to the outside. You want to have the best leverage for the heel strike you can get.
- what I like to do is to initiate the move with heel strike, to get the torso moving towards the side and when the torso is just moving, I pretend to squeeze my elbow to the torso and drive it to the ground as hard as possible that engages the lat, rhomboids and rear deltoids to pack the shoulder.
- when getting down place your free hand a bit more away from your body (more like in your first video, in the second video your elbow lacks space for leverage and your shoulder then literally gets crushed) then try to push the floor with your hand and then with your elbow away from you which will help shoulder packing
what is really helpful, is to practice just these cues on a few consecutive reps, roll to elbow rolling down, roll to elbow rolling down...deliberately and slowly. I will bet with just a bit of practice Your leg stays on the floor even with the 28k and your shoulder stays packed and the other elbow stays locked out.