I've only had fleeting contact with the homeless, just passing them on the way to work, but they do seem to cover a wide range of types. One I may have mentioned used to dress in floral patterned, home made pants, a suit jacket and wear a Sombrero!
He 'lived' at and around Central for years. He used to sleep on the trains. He was a lovely polite old fellow and the platform staff all knew him and used to sneak him into a spare, unbooked compartment of an overnight train for a good night's sleep, a shower, and free brekky and he'd be gone for a couple of days until he got another freebie ride back. He was rattler rider I guess, but did it in 5 star style.

He was the only one ever got away with that trick that I heard of so I presume he had some links to staff from former days or something.
I was in gossiping with the switchboard girls one night when one got a call and yelled something like 'you have to be bloody joking!' and pulled the plug on the call. She was outraged that it was someone calling to tell her that he'd got a bed at the Matthew Talbot doss house so would she tell 'Fred' he could have his usual seat on platform 1 for the night. "Do they think we're running a bloody hotel for them or something??" It was hilarious. They had networking down pat.
Another regular was a very black man, Papuan perhaps, who was always quite well dressed and would nod and smile at us as we passed. His 'bedroom' was a niche near the door we used so we saw him often. More than once I saw the patrol cops bring him a cup of soup or coffee or something and sit on the ground with him for a chat. Must have been 'history' there too.
One quite elderly man who'd turn up occasionally, used to paint all night. He'd turn up with a piece of board, sometimes just cardboard, that he'd picked up from a skip, and prop it against a window under a light. Then he'd bring his paints out of his bag and in the morning there would be a finished painting sitting there. He just left them behind for whoever wanted them. I know where one is.
A bloke I worked with came in all excited and said "he's painting a sailing ship!" Rick went down before dawn and waited for him to finish it, slipped him 10 bucks and loaded it in his car to go over the new bar he was putting in. He said the old fella didn't want to take the money! He was just happy that someone wanted his painting. That sure doesn't fit the stereotype of the homeless does it?
Maybe he wasn't homeless, just eccentric, we never saw him around during the day. I had a look at the painting before we drove off for home and it wasn't the best I've ever seen but it was as good as most. It was even on an unchipped piece of board. Bet Rick's still got it, he just loved it.
Still, that was all long ago now, the homeless aren't just drunks and eccentrics these days I guess.