> What gets them in trouble is the clever hacking, not a fundamental moral flaw.
I think you've got that backwards. Crims gonna crim. A clever hacker will evaluate ALL the risks, whereas a moral flaw blinds people to risks. Doesn't mean somebody can't have both attributes.
I quite literally stole an education, and there's a college transcript to prove it. I was a clever hacker, and I worked hard; I was aided and abetted by the college administration, inducted into the Masters candidate ghetto as an honorary member. When they made it a felony I quit that path, and following Hunter S. Thompson's advice [0] I went into business so that I could continue learning "on the job". (Nowadays they call it "OPT". Served today with a very thin glaze of sarcasm.)
During that tenure I met people who wrote theses for a living, who appreciated my industriousness and offered to admit me to their fold. I drank with foreigners ("muslims") who wanted information I might have or be able to obtain; I suggested that they get their home countries to forge documents and and then get admitted as students.
I've quit jobs after an appropriate "honeymoon period" when I still hadn't been furnished documentation demonstrating that we had customers' permission to be doing what we were doing. I've quit jobs when government compliance was considered a game rather than a minimum standard of performance. [1]
I pass government background checks just fine; no reason I shouldn't. I get the "dgaf" attitude, but I strongly suggest getting it in writing. Doing things off the books is a cancer; and it's contagious, like that 10,000 year old dog cancer which now moves from host to host.
[0] "When the going gets weird, the weird turn pro."
[1] If you need somebody who takes risk assessment seriously, we should talk.