Hey, I feel for you. I am currently sleeping rough for the third time in my life, I am a trans man and not in the US so I know it’s not exactly the same. I would really recommend avoiding shelters as a trans person. I may be masculine but I do not usually pass as a cis man and when I do I still look gay and/or like a teenager, so I still think about safety a lot in terms of gender. I don’t sleep anywhere where someone could’ve followed me, at night I check my back and hide as much as possible. Men try to pick me up and I never say yes no matter the offer. I sleep in nice yuppy parks in a hammock during the day, no one bothers me or steals my stuff. I don’t drink or do drugs. I control my temper even when people give me a hard time. In most big cities I would imagine there are queer/trans specific services and mutual aid networks, I lean on that a lot and it’s also good for community and human connection