This is unnecessarily cruel but I understand the frustration with this sort of thing. A guy falls asleep somewhere he shouldn't once, fine. Ask him to leave when its time to close up. But some of these guys will pick a spot and post up there for years, harassing every single customer that walks by. In my city there is a certain restaurant I refuse to eat at simply because I know exactly who will be waiting at the door. He has been there day in and day out for at least two years now, and he simply will not let you go in or out without repeatedly asking for money and getting rude with you when you decline. Its like the opposite of a greeter - its somebody who goes out of their way to harass you every time you walk in.

There's a bad homelessness problem here and that's just the tip of the ice berg. Cracked out hobos roam the halls of local universities trying to intimidate broke college students into giving them money they don't have. They post up outside of your office building and block your exit so they can give you a sob story about why they need your money every single day, even as its painfully obvious that they're so high they can barely stand. They are shameless and relentless. I feel no sympathy for them.