I've been homeless for almost 2 years now. It's very depressing at first and learning to survive is... tough, to say the least. It's harsh being homeless. I consider myself lucky to live in a somewhat large city, there's lots of places to scrounge from but enough space for me to stay away from the dangerous hobos and thugs.
I think you would be better off applying for welfare to be honest. I consider myself too far gone to go back; I don't think I could live the life I used to before I used up all my money, there's just too much to do and too many things to keep track of.
I think it took me over a full year to finally say I am good at surviving the streets. I don't recommend doing this, I've been close to death far too much for my liking and the amount of times I've been injured or an inch from being seriously injured is too high to remember.
Think of it like walking on hot coals, but there are walls and a ceiling too made of hot coals, and the ceiling is falling apart. It takes a while, but once you make it to the other end of the room you find yourself at a shit-stained palace made of trash. But after walking trough the room of hot coals, it's a sight worth crying over.