The homeless aren't as hapless as ya think. Their survival instincts have been sharpened to Still Bay Points. When they are tired they sleep.
Here's the deal. When you have something to do, don't stress it. Work with it. Here's how that goes.
Late afternoon a local boy, photographer great, Martin Schoeller, came to shoot a portrait of a lovely couple. But on the loading dock of the Sofia Storage Co. Schoeller's team faced an existential quandary. Although they had secured the permissions to make photos in the spot occupied by a nearly naked man counting ZZZ in fashionable polka dot socks, Schoeller didn't expect to have him in the picture. The videographer turned on a leaf blower in front of him and it made no impression.
My theory for working on the street is thus: if cooperation isn't possible go for incorporation. I climbed up on the loading dock and photographed the man dead to the world and began flying around him, my grandson in tow. It was clear there was zero consciousness. And so it was a sign that the coast was clear. Take your pictures. The subject is down and out: cold.
From there the shoot went without a hitch. Everyone was happy. No disturbance. When in doubt let the sleeping men enjoy their time to dream.