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Dr. Phil speaks with Kyla and her husband, Andrew, who claim that, despite both working full time, they are now homeless and living in their van due to the rising cost of rent. Then, meet Simon, whose story went viral when he shared in a video that he was secretly living in his company’s office building after he says he found out his rent was being raised, at the same time the pay raise he expected didn’t happen. Dr . Phil also meets Caleb, a YouTube and TikTok personality living in New York City, who has been documenting how people are living in and around The Big Apple. Caleb gives Dr. Phil a tour of some of the smallest apartments in New York’s five boroughs. And, meet J.R, who says to afford being able to live in New York City, he is forced to live in a 95-square foot studio apartment with a communal bathroom . Lastly, Stewart Silver says he has created a safe place for working homeless families but now is being forced by the local government to evict them.