Like thrift stores, free food, shelters, panhandling, public transportation, wooded areas (for sleeping), public toilets?
Presumably, a lot of people feel the answer is "San Francisco." I've never seen so many homeless people given free rein in a city. The situation is bad enough that I would avoid living there for that reason alone, despite everything that's wonderful about the place.
The homeless in SF make the city all but intolerable, R1.
Key West, Florida. Homeless shelters and soup kitchens galore, perfect weather, and an endless supply of leftover alcohol and tourists to rob.
A small town that didn't have too much of its economy tied to factory jobs that no longer exist
thrift stores, free food, shelters, panhandling, public transportation, wooded areas (for sleeping), public toilets
Check, check, check, check, check, right by the river, and check. Don't forget "Street Yoga" programs for homeless teens.
Portland is great for summer and fall, but not for winter. Wet and cold.
Honey, the best place to be homeless is Florida. It's not only warm, but you can eat fruit right off the trees.
Portland has a new building specifically for the homeless (showers, lockers, transitional housing, etc.) that really is among the nicest new buildings in town.
Santa Barbara seemed to have a large homeless population and I assume they're there not just because of the beach but also good services, wealthy residents, etc.