I am not the best chip player here by any means, but i did read the part about chipping and pitch strokes. Watched the video's.
My personal take is never chip a shot unless on the fringe within 25% of the total distance to the cup from the edge of the green, and never if penalty lie is over 25%.
The auto caddie is a notorious lier, and will sink your efforts to play a good intelligent short game everytime. Never just take the auto caddie's recommendation!
Most of my short game is with wedges, either full, shortened up to not more than 75%, punch shot, same 75% rule, and the flop shot. As with any stroke it is imperative that you hit the dinger. Unless you have clubs with a lot of "forgiveness"
The only club I own that will allow me to go under the 75% rule is my shortest wedge. Even then accuracy and distance will be less than optimal. Hope it helps. My Nickle.