I believed that I will end up homeless when I was a teenager. So when I was 17, I made a test run and lived 4 days without money on the street. I didn't beg but I asked in bakeries for old bread and they gave me croissants from the morning which were a bit chewy, I also searched trash cans from shopping centres and found a few eatables. Finding a secret spot to sleep was the hardest part. I climbed on a roof of a school or slept in an empty trailer behind a factory. When I reached the countryside I helped a farmer for food and a place to sleep. It is challenging, I recommend trying a test run. Maybe with more experience it gets easier. I think being a drifter is easier and more fun then being homeless in a city.