When I worked in "the loop" of downtown Chicago I'd walk a mile or so from where I parked my motorcycle to the office @ 1 N. State.
Every day I walked past the same people pan-handling on the same corners. Many had signs with invented stories to try garner pity from suckers, stuff that was obviously fictional to anyone who had been walking past these people every business day for years, like "Stranded traveler, need money for bus fare" kind of stuff.
One day it became clear why some stuck with the stranded traveler story; it enabled them to wear normal, even classy high-end clothing, and not even have to be dirty-looking. On that day as I walked past a woman doing this I noticed she was wearing a new pair of some exceptionally fancy shoes, and the price tag sticker was still visible on the sole: $499.
On another occasion, I recognized one of these people but off-duty, crouched against the exterior wall of Sears trying to light a cigarette with a match, with their wheeled suitcase parked between themself and the wall. It was windy (Chicago) and I had a lighter, so I went over to help them with a light and as I got close enough to reach their cigarette I saw inside their "stranded traveler" prop suitcase they had left open: it appeared to be full of cash. Another pro for the stranded traveler gimmick: it gives you reason to have a suitcase to hide the sizable stash.
These folks probably weren't homeless, they just earned an easy living by acting like they were in a relatable bind of a situation to fellow tourists in a busy city.
I got to know someone who lived homelessly for a few years on the streets of Chicago, and he said real homeless people in Chicago are easily identified by their clothes and possessions being bleach-stained. Apparently the municipal crews would spray down the encampments on lower wacker where they'd stay warm through winter, without warning. So people who slept down there would have all their possessions/clothing ruined by the bleach. This was decades ago, I don't know if it's still applicable.