I would be interested in their background. I don't think 500hrs even remotely makes you into any kind of sky god. I've just passed 1k hrs, since 2001, and I like to think that when I fly manually I fly accurately, within 100ft generally. The ATP who did my BFR the other day said I fly to ATP standard.
And I don't know any owner-pilot who does even half-serious touring who is as sloppy as those you have met.
There are also many 1k+ hr pilots who have accumulated this over say 30 years, and many rarely fly nowadays. Their skills will erode, but if they stick to Sunday VFR they aren't going to generally kill themselves.
There are also many pilots who do only a small fraction of what they claim. Some are readily found on pilot forums, but not all. The other week I was in a group of pilots (abroad) and one chap made a fantastic claim on how many trips he had made between a particular pair of countries. The rest of us looked at each other discreetly, and instantly worked out he was exxagerating by at least 10x. Yet, despite his obvious intelligence, he thought he could get away with such obvious bullsh*t, and in a group of people who can most definitely add up. So a lot of your sky gods are probably talking bull and some may even have forged their logbooks.
As I mentioned earlier, a lot of professional people find things a bit hard when they start to learn to fly. If you are reasonably successful then you are probably well organised and - not in my case but often in business, especially if you are young - pretty aggressive. At the far end you get some cocky d1ckheads....
But take someone who is just reasonably good at their profession. They walk into a flying school and what do they see? I don't need to answer that, do I? Much flight training needs an overhaul. I don't think it is the age of the instructor as much as the way the whole thing is set up.