Backpacker raises a few valid points in general (I have no knowledge on the Reno crash, and no comment to offer specifically in respect of Mr. Leeward).
Pilots who are "familiar" with a type of flying or an organization can tend to blur the boundaries of the paperwork, and be tolerated doing so. It's a possible failing on both sides. The pilot wants to fly again/more (we all do), and the organization wants to encourage their participation in general, or at least not seem unwelcoming, so as to scare/anger others off.
I used to organize a local floatplane fly-in/airshow, which met the Transport Canada requirements for organization and control. The fact that we advertized it to the public at large was the line crossed to make it an "airshow", and subject to regulation. That same event continues to this year, but only as a "fly-in" now.
Anyway, we used to have pilots turn up for "the games" on the water - planned challenges for flying skill and maneuvering mostly on the water, usually timed. Everyone had to register with me to participate. Registering required the presentation of all of the valid paperwork for the pilot and aircraft.
I found three types of people: Those who were totally compliant, and had the paperwork to prove it, those whom I knew were not compliant, but never registered, and those who thought that they would participate without the paperwork. Many pilots would present themselves to me, and not only not have the paperwork, but actually admit that they did not have a pilot's license/C of A/insurance etc. I said to several with some surprise in my voice, "do you realize that that guy over there is a Transport Canada inspector, who's watching what's going on? You should go and hide!".
Now, when I know I will be flying someone else's aircraft, I try to "push" my paperwork at them, so they don't have to pull.
I know a lot of senior pilots, whom I admire immensely, and continue to learn from. I have notice that they tend to self regulate the types of flying they do so as to be less demanding in several senses. Something about superior judgement instead of superior skill (and stamina, I suppose). One more reason I respect them....