I haven't been homeless, but I've been desperately broke and unemployable. I lived on a limited income that didn't stretch the entire month. All my dishes had broken and I couldn't save enough to buy new ones cause I had to keep buying paper plates for my meals. My mother bought me dishes for xmas and it was one of the greatest gifts I've ever received because it freed me to start saving a little bit each month.
It costs more to be poor than it does to be rich. It's a never ending cycle. You can't go to CostCo and bulk up on frozen foods if you have no electricity to keep them frozen.
I don't know how we can simulate conditions for everyone to understand the plight of homelessness. I'd want anyone and everyone who thinks that homelessness is just people making bad choices and being lazy, to go live in a tent in 30F/0C weather for a week getting kicked out every other day and try to hold down a job.