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Just to offer my own anecdotal experience, in all the homeless people I've given care packages to (info on how to make your own here), I'm fairly positive none of them were faking it, since it's pretty difficult to fake sun burns, sun tanned leather-like skin, missing teeth, etc.
I've only had one person turn down a care package (which have no promise of money in them), and that's only because he already had enough supplies at the moment and couldn't carry more (he also wasn't asking for anything or holding a sign, I just offered).
The rest were very clearly extremely grateful just to receive shelf stable food, water/flavored drinks and some toiletries.
All that to say, most are not faking it (especially with how many people are losing access to housing due to how insanely expensive it is now, plus all other cost of living), and it is very much worth assuming the best instead.