Hi and thanks for the questions.
1. To be clear, I'm not advertising on Olx saying I'm giving away money, so I don't have adverse selection to deal with. Rather I use to the "Seeking Work" section to proactively reach out to individuals that seem like they might be in need. And when I do reach out, I don't just open with "Do you need help? Can I give you some money?" Rather I try to build rapport and develop a real relationship. Most of the people I contact are just excited about talking to an American even before money enters the picture.
So I think the remaining risk isn't that the person isn't who they say they are but that they'd exaggerate their circumstances to get more money from me. The way I counter that is by developing a real relationship with the recipients. I talk to most of them on a daily basis. See pictures of their house and children. Get their whole backstory. And, in general, just end up with enough collateral documentation about their lives that it'd be hard to fake.
And, in fact, it's these relationships that are the most rewarding part of the whole thing. You're not just helping an abstract stranger. You're helping a very real person that's become a part of your life. My first recipients, the single mom, has become something of a sister.
2. I don't use M-PESA directly. Rather I use WorldRemit (https://www.worldremit.com), which connects to M-PESA, to send the money. Other than the occasionally delay, it's a pretty seamless experience. When you factor in the poor exchange rate you get, the cost of sending money is about 1%.
3. Honestly, it's just more rewarding to give directly. I know keep saying this but to talk to the recipients and see how grateful they are and how life changing the money is just an amazing experience. And it's motivating. I want to keep giving and find ways to give more.
As for the handout question. None of my recipients seem to attach any stigma to receiving the money and none of them treat it as a handout. They all keep working in one way or another and most use the funds to start a business of some sort.