There’s two type of pilots in this world... the ones that have failed a checkride and the ones that WILL fail a checkride. If you can do it the sooner the better 😂😂

Failing a checkride can depend on the mood of the guy doing the checking. Then you have the people who never bothered to become a CFI who also brag about not having any failures.
It's all subjective. Another issue is the computer firewall that blocks your application from moving forward because of a failed checkride, which does not care about context. That's the reality of things, so I suggest having the fewest amount of check rides and not becoming a CFI, so your app is more competitive. Sounds stupid because it is!

Isn’t Mesa the go to airline with multiple failures?

At this point they all are.

This is a good way to see things

The fact that failures seem to be some weird acceptable norm is disturbing. However it is a proven method of pilot retention..

Lol. Far from the truth.

I also did checks for my 141 school. I can’t count how many times I got calls from the instructor of a student that failed and got an earful for failing them for “one thing”. The fact was that may have been the thing that pushed it over the edge but there was multiple things before that.

The point is I’m sure they’ve heard it all before. Regardless that your story is legit or not. They’ll just default back to the “here we go again” mindset, that others have caused before you.

As it was said before. You’ve gotten yourself to a good position with your gold seal and check pilot status. Use those prior failures to set your platform. Everyone loves a good comeback story. Then when you do get to a regional, do your best to keep a spotless record and set yourself up for the next step as best you can.

and Skywest. and Envoy. and Endeavor. Etc etc etc

Far from the truth