An interesting thread. Not to add fuel to the fire, but here in NYC it's sometimes virtually impossible to distinguish between the very rich and the homeless. Sometimes you need to look closely at their hair, skin, and general appearance of health (or lack thereof) to know for sure. There are plenty of rich eccentrics here (as there probably are in other urban areas), who could care less about what they look like to other people: if money's not an object, why give a #$%^ being the general rule of thumb. I would maybe look twice at a homeless looking person riding a bike here, and then make one of two conclusions:

1) stolen bike
2) a person rich enough not to care about their appearance, riding his or her Rambouillet.

So maybe what we have here is a case of judging the book by its cover, so to speak, with an clear lack of actual facts to support the "homeless" claim.