This is just his character, all the companies are pushing this for him, it's kind of like pro wrestling these days. I don't buy it.
I don't know if he was homeless but he was a ward of the state and live in different foster homes. This was on one of the vids done by Palumbo who visited him where they shared a home cooked talapia dinner. He was living in a housing project where Palumbo commented on the urine smell in the elevator. Kai's place was a crappy studio apartment. Plaumbo got to sit on the couch whereas Kai ate standing up. And this only about 4 years ago or so. I think he really started to make money after winning the New York Pro in 2008 and then the Arnold the next year when sponsorships started coming in. Oscar did help him a lot in the early years.
Jay wasn't necessarily a golden boy but he grew up in an upper middle class family and got his pro card at 21. Sponsors jumped on him as he was the perfect image: white, good looking, had the "golden boy" look, clean cut, well spoken, married high school sweet heart.... He never was hurting for money.
I don't like some of the stuff Kai did but when you don't have money. When you literally don't have enough to buy food, you get desperate. You have live. You have to survive.