I have thought about this a lot, but I haven't done it. In my experience most have phones. I guess just offering a donation via LN? The problem in the US is that the feds have scared off the easy onboarding custodial wallets.

I think there is just one thing (except offering free knowledge and guidance) we can do to really orange-pill homeless people. Give him/her or even them a possibility to exchange Bitcoin for cash for market rates without fees. This way, homeless people can accept Bitcoin donations and actually use them to make purchases. We must consider that more than 95% of the expenses for homeless individuals are for things that, unfortunately, cannot yet be paid for with Bitcoin without going through third-party providers and incurring fees. However, this is absolutely not an option in the specific situation of almost all homeless people. Additionally, if we assume inexperienced users, they are very likely to fall victim to some kind of scam along the way.

Therefore, in my opinion, the only viable solution is to offer an exchange at market price without fees or KYC. I have already done this several times and now have three homeless individuals who regularly come to me to exchange small amounts of sats. I even round it up to a neat sum. However, I notice that the amounts they receive are slowly increasing over time. But unfortunately still far away from decent.

Access to money/savings that doesn't steal from you over time is still pretty high on the hierarchy of needs.

Someone without food or shelter or community likely also has mental illness, antisocial behaviors and/or substance addictions.

Sound money is the furthest thought in their mind.

You might be thinking, "well if they just HODL a little bit, BTC could help their situation."

Unlikely. If someone has the fortitude to HODL and do research, they are unlikely to end up homeless in the first place.

BTC is most attractive to productive people who work hard and feel they are getting robbed by inflation.

BTC needs more productive people building things holding and championing it. We have enough NgU freeloaders already.

None. "occult, mind control, toxic food, bitcoin, the 7 sins, etc." might be some of the last things on their mind, whereas food, water, a safe-ish place to sleep and (likely) their next hit of whatever drug they're coping with will most likely be the very things they do have on their mind.

You may be right. But the homelessness is chosen one. I think these people should strive for work. They can obviously find some.

Well, most homeless have cellphones but unfortunately their stuff gets stolen often. But this idea might help them protect their stuff even more. This is a great onboarding and evangelism idea