If the housing market keeps going up, where's the risk? You'd have to be the dumbest man in NYC real estate to lose money like the president's son-in-law. Small time landlords are a slightly different ballgame, but it's still bizarre that we allow individuals to speculate on where people live and and extract money from the less wealthy in this fashion.
EDIT: Also, what other job requires work up-front, but then nearly none? Landlords are famous for terrible upkeep. Even in communities where problems are generally fixed, most of the time, the landlord just collects a check until a problem pops up. They only have to work for rare serious problems and for managing move-in move-out.
EDIT2: The craziest thing is that we see that they do this and still collect 25%+ of ordinary people's incomes for an invisible service that is merely holding intellectual property. It's as though people pay to live in a castle keep with no services, pay the local lord, and justify giving 25%+ taxes on top of what you give to the actual democratic government (typically less to much less) because the lord is somehow a great symbol of the economic system.