Whelp, you could always try red loctite if you're feeling bold/confident.
The steps GM noted to torque this bolt do indicate the bolt is a torque-to-yield bolt (initial torque set, then based on angle as final fasten), but the GM bulletin you linked to should have also said something like "you cannot reuse the original bolts once loose" or "one time use only bolts" - but it didn't which is strange.
If the lock washers you were using had a larger diameter that the bolt head/nut, that would distribute the force over a larger area and you may not be getting the actual clamp load needed at the bolt head. I actually used to be an engineer at GM way back in the day and would not add any additional hardware (like star, conical, or lock washers) to a joint that didn't have them in the original design. Just a thought.
You could also try nylon lock nuts on the back side, but I am not sure if there would be an interaction issue there if you used loctite contacting the nylon at the same time, something to research.
As for the 110 degrees, just get the first pass torque achieved, then use a paint pen/magic marker to note start position across the bolt head and frame, then make a mark on the frame where 110 degrees would be, then go as far as you can with the torque wrench, remove it, reset it while keeping an eye on when the paint pen mark on the bolt head reaches the final 110 degree position, even if it takes 2 or 3 times pulling the wrench off and you can go as slow as you want.