I've been homeless multiple times, thankfully never rough sleeping yet. Employers have always been an issue because the system is built around the idea of you living with the family or being able to go back to them if you fall on tough times: without that, any form of thriving is more frequently than not out of reach.
I had to move countries multiple times purely out of necessity due to the housing crisis engulfing possibly everywhere, but you can try to hop around, it worked out temporarily for me, but the alienation due to friendship loss and language barriers are soul crushing.
I am currently going back to a country where I speak the language of, even though it's near guaranteed I will be homeless rough sleeping there (I moved countries to avoid it, but I cannot take living where I ended up).
People like me I knew growing up ended up with severe mental issues. Some resort to sex work, some are on government money. Some aren't with us any more...