And since homeless people are actually homeless, without a fixed address, Amazon might not know where to find them. But, as you say, at least he doesn't have to interact.
Sarah91, did you watch the video? He addresses this. He asks the person for their name and what they need before he places the order. Then he includes their name and a description of the person in the special instructions (along with street address for where they are located), and apparently Amazon will make the delivery.
I think he specifically drew in some of the reasons people can’t simply walk into a store, track down the items, and return to deliver them. You take one minute to check in with someone, find out what they need, order it as you walk the rest of the way to work - arriving on time - and Amazon takes it from there.

Convenient kindness. Plus then you have time to make a video and maybe remind someone else with kindness in their heart but little time to work out the details that the tools you have in your utility belt of provilege can make a help you make difference for someone.
What #2 and #3 said.

It seems like Herzog may have not watched the whole video. She says "but that would require actual human interaction," but dude asked the people what they needed and got their name and all that. He just didn't have time to take the bus to REI and pick up the gear, only to have the homeless folks be gone by time he got back.
Self Aggrandizement.
Why is the guy sitting on the sidewalk? Oh because he's homeless. No need to look for housing or a job. Just sit on a sidewalk and get a delivery.
Why do people have to go out of their way to make an act of generosity known to everyone in the world? Do the right thing for the sake of doing the right thing: not to pump up your own ego. It's a little disgusting and low class

Great. Now the junkie tweakers can run faster.
I'd say the point about human interaction is well-taken. And I'll take that point after I do shit for the homeless, which I haven't.

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