I was briefly a couple of times, MB. Sleeping in my car for a while; luckily it was a full-size 78 Dodge sedan and not a compact but even so....
The other time I was "kinda" homeless. Working a crappy convenience store night shift job with only an old motorcycle for transportation (yes it was wintertime and yes it rained a lot) and a friend of mine let me crash at his apartment. Thing is, the only space available was in his utility room so I slept on the floor in there next to the water heater.
Being without a place to live, not being sure when you'll get your next meal, being truly poor, that can be a good experience if you learn from it. It can make you more determined to succeed and never go back there.
Mike.