Help with All in order Progress

Alright this million $ bonus is halting my heist progress. I was curious and joined through Lester as a crew member for my first heist, after purchasing my first apartment. I completed the flecca setup and heist, and a few setups for the prison break... but now I don't know where to continue without losing my progress.

Do I have to join as a crew member for now own? I think my progress stopped somewhere between setup-heist of the prison break. So Anytime I try to be a leader of a heist it immediately gives me the lose all progress message. I'm starting to think the million isn't worth it, but it would help for the buzzard.

I keep doing the setup where you steal the car in the container, steal the bus plans. I've completed it multiple times, but does a more recent fail effect your progress ? I'm confused with this and wish they offered a "how-to" for such a big challenge in the game.

Any help would be appreciated.