Same exact thing happened to me last month on a rear quarter on an older Camry. Cracked bumper cover had a soft push in it right above the wheel and my puller kept slipping off because there was nothing solid to grab. Hit it with the heat gun for a bit, worked it from the back side with my thumb and it came right out. Customer never even knew it was there. Totally agree on where you draw the line though, once you get a hard crease or it is anywhere near a seam or a sensor, that plastic gets thin and you can stretch it or burn the paint before you know it. Shallow and soft is the sweet spot, anything sharp or deep I am still pulling the panel.

Weighing coins on a scale sounds like a great way to get written up if anyone ever audits you.

That parking lot test is real, I did the same thing after leaving a call center job and it hit me how tight my shoulders used to get walking in there. The "nobody panicked when I asked a dumb question" part is huge, that alone tells you you're in a better spot. Give it a few more months and you won't even feel the need to drive by anymore.