man I saw a homeless guy in San Juan Puerto Rico, chilling on a hammock next to a lagoon with his dog lying next to his side. ever since then I thought that would be my destination if I lost it all.
there's probably a decent hobo community in San Fran -- but it's so cold and wet. Honolulu sounds interesting.... but I think I'd drop the shopping cart. Too much irony there.
I'm pretty sure the cops would throw you out of the country. If you're lucky, it'll be over the north-western border, not the south-eastern one.