Where was Bennett getting his money..
He was paying for expensive hormones treatments and top surgery, plus having his own apartment, etc. He did say at one point he worked at a photo shop, but that seems like a low-paying job you wouldn't be able to finance all of the things he had and was doing.
I knew someone - as well as myself - who worked in low pay and she was forced to live in cars sometimes, and sometimes with family. She claimed to have had a mental breakdown and then managed to get SSI benefits and that was the first time she said she was able to afford her own place once she got on government assistance. She is male-to-female and Medicaid paid for her hormones. I don't know how often she was able to afford any of that when she was working.
It's my belief that since Bennett was attending college that he was getting grants and loans and that was how he was staying afloat. I've heard a lot of people do that. Sometimes they do it when they are waiting to be approved for disability, but can't work so they come up with clever and crafty ways to get money.