His best shot at getting a job is going to be through networking. Having a friend somewhere that talks to the chief pilot, and brings him in that way. Other than that, like was posted above, with a stack of resumes in front of me four failed check rides is going straight in the trash. If he can't pass any of those, why would I think for a second he'll succesfully complete training and not waste my company cash? Too risky of an investment.
Reading your post I see four busted check rides and a lot of excuses. You "reprimanded" a DE? Maybe if he gets his CFII/MEI and spends a few years as an instructor with a flawless pass rate, that may bury some of the past performance, but having dreams doesn't mean he's capable. You'd be doing him more of a favor being honest rather than him continuing to throw good money after bad.