You cant compare the 80's to today. And even then, they still did goofy things with non wrestlers (Fink, Gene etc). Vince was very against putting himself in the ring until Lawler convinced him to do an angle in USWA in early 90's. But you cant be critical of Tony and ignore Vince putting himself in angles just because Vince did it 10 years into his run rather then year 1. Its a common thing in modern wrestling to do goofy things for the live crowd. That wasnt the case in the 80's. When WWE did angles with Gene and Fink, it was on the live show, not "dark".
Nothing I've heard about Tony indicates he's a money mark. Hes a smart guy and has a lot of other smart guys around him.
Dark Order is a mid card gimmick. Wrestling, including WWE, have a long history of out of shape guys. Hardly an AEW thing. The whiffed punches was horrible. It happens when using locals as extras sometimes. I guarantee they'll be better vetted next time. Since you obviously didnt see it, that whole show ending angle was terrible (there ya go).
Who was the biggest money mark locally (that didnt get in the ring). In terms of promoters getting in the ring, you're conflating money mark with wrestler/promoter. And you're subtly buyring all of them with remarks like "living their fantasies". When an active wrestler is also a booker, they either book themselves too strongly or not strongly enough. I generally disagree with the practice but most indies are started by active wrestlers so what are you going to do.
Outside of Ernie Todd, I cant think of any local promoters who egregiously put themselves in the ring (refresh my memory if Im missing out on anyone). Wrestling is rife with examples of non-wrestlers doing angles/matches and there is nothing wrong with the concept inherently. The execution is a different matter...
ECW had a lot of bad workers. Lets not romanticize it. RVD was arguably their biggest star and he was as green as a wrestler as he was great athletically for a long time. What Paul did that WWE and WCW didnt, was give small great workers a shot (especially from Mexico & Japan when the big promotions thought they wouldnt draw in the US). But those guys were quickly scooped up by WCW.
But WWE and WCW didnt horde talent back then. WWE has a massive, massive roster, some of whom they keep for the purpose of keeping them from AEW. Talent also wasnt paid like they are now. AEW has a really good roster but they've been on TV for literally 3 months. Their roster will get deeper as time goes on and contracts come due.