Good points, but an important thing to consider is the Jedi - Obi-Wan and Yoda included, Yoda especially - were so caught up in their own hubris that they allowed all these events to transpire in their faces. The rise of the Empire didn’t cause this to change, as evidenced by your points that Yoda and Obi-Wan lied to Luke until they realized they couldn’t anymore. Plus, they did the same to Anakin and Ahsoka in different situations during the Clone Wars - while they all were still part of the Jedi Order. So I’d say the surviving Jedi barely changed in that regard. But my point was, Obi-Wan never fell to the dark side as Anakin did - despite having gone through worse for longer.
Personally, I hope future Jedi are more pragmatic / Grey in their approaches, similar to Qui-Gon or Dooku before his fall. I think if more Jedi had been like that, Palpatine would not have been able to be as opportunistic as he was. Btw, thanks for engaging in this lol I’m a sucker for it all