I have not gotten any offers to take the other side of my 10:1 offer...
Anyway, I'm a bit of a JWST pessimist too, but I don't find any of your arguments very convincing. It feels like you're cherrypicking bad things about the program without doing a very good job quantifying why they're supposed to matter in the big picture of absolute risk.
The sunshield is a crazy idea and no one challenged it. Even worse, it is impossible to test it on earth. Just about every (partial) test of the shield has revealed problems that have been patched instead of starting over. If they had made the Webb telescope nuclear powered, many problems would go away - including deploying a 5 layer, experimental sun shield.