In my ideal scenario, I'd still have money, I'd just get a check from the guvment and not have to work. But that ain't happening, and until gas, food and cigarettes are free, i gotta earn some cash.
You don't have to work year round. You can work seasonally, live cheaply and use money when you need to. Being desperate and hungry ain't living free to me. Having to hope you get enough money from spanging to eat ain't free, neither is worrying about cops running you off or hassling you.
1000 dollars can be stretched a long way and gives you a security blanket. You can make that much with a minimum wage job in about 4-6 weeks if you save most of it. Live cheap and spend the money to help you reach your goals, travel, do whatever. It'll make your travels a lot more enjoyable when you can't find any food, need to upgrade to a better jacket, need to get somewhere that hitching/walking isn't going to cut it, whatever. When you run low, work another job for a lil bit, quit, do your thing, whatever it be, and work again when you need more. That would be my happy medium anyway. I see that route as neither being a slave to a job or to poverty.