I learned more per minute from my ex-military examiner pilot for instrument, commercial single engine, and commercial multi checkride than my instructors per hour at that point ( after private). He wasn’t so much trying bust you as make you better. He had me plan an instrument departure that went on instruments right after takeoff out of El Paso in a direction that could easily have been a collision with terrain, for instance.
Lesson: get to know the every airport and it unique features, terrain, etc personally. If you hear about an accident near an airport put it in your memory as something important when you think about that airport.
Just like frequencies, make room in your mind to know them personally.
Another thing on the commercial, he told me to descend immediately to xxx altitude and heading so and so, then said the way I did it would scare passengers.
Put me in a spin under the hood on my instrument, which was no problem but good experience.
I consider him a mentor although he was only my flight test examiner.
Also, when you are a looking for a pilot or flight instructor, if you knew enough to pick one you wouldn’t need one! But you can look for some silver hair.
Everything you outlined sounds like just that, something to make you better, rather than busting your chops.
I am a huge fan of Bill Whittle, who is a pilot and aviation enthusiast (not to mention a staunch and vocal conservative with his own podcast) and when he started out early on learning how to fly in a glider, he was practicing breakaways which they were doing at a minimum altitude of 500 feet.
He wondered what would happen if he had to break away at 200 feet, and asked his instructor if he could train for that.
His instructor did a rapid assessment and given the quality of his student, agreed to let him train for it.
I really liked that mindset.