I personally try to not be flat broke, especially bc I have a dogter to worry about. Makes u feel like shit when u have no money, there's no decent food in the trash, and ppl are standoffish bc they're sick of the homeless in the area and u gotta eat mayo packets from the gas station for dinner.
If u can bring a couple hundred as back up for when u can't steal, no good trash food, and strangers won't give u the time of day it'll make ur life a lot less miserable.
U should have the option to not spend money plenty of the time if ur willing to search for food n steal tho. Plus if ur sitting outside w a pack ppl will sometimes just give u money without u asking. Hopefully that can go toward new socks, fuel or other supplies, the inevitable "I'm so sick of standing on this on ramp for 3 days fuck this I'm taking a bus" etc.
A good idea is to bring pins/buttons/small drawings or other lightweight craft to sell when ur sitting outside "for a donation" or when ppl ask what u do for money (u will get this question from almost every car that picks u up). When I ask for a donation when asked how much something is ppl often give more than I wouldve charged for a button or whatever anyway.
TLDR: bring money if u can but it should be pretty easy to not spend much if u are serious about that n not lazy. Ppl will give u money for existing outside. Consider some kind of hustle.