You could say that Michael Bloomberg's homelessness problem goes back to 1981, when a series of municipal lawsuits made New York the only U.S. city to guarantee a roof over every one of its residents' heads—and gave the city's mayors the job of funding that guarantee. Since then, successive administrations have struggled to manage an ever more unwieldy shelter system, each to its own degree of controversy and failure.

In 2004, then-first-term-mayor Bloomberg pledged to wrestle the beast down to size. Over the following five years, he said, he'd shrink the city's homeless population by a full two-thirds, using a combination of targeted prevention initiatives and behavior modification programs aimed at making homeless New Yorkers more accountable for their own transitions into stable housing.

At its launch, the Bloomberg plan was well-received by much of the city's homelessness advocacy community, which lauded the mayor's ambitious goals and his emphasis on prevention. But the honeymoon ended quickly, starting with the mayor's 2005 decision to reduce homeless families' access to federal Section 8 housing vouchers. Advocates have spent much of the past term-and-a-half wrangling with the Administration over efforts to put time limits on rental subsidies, charge fees for shelter stays for those in shelter who have income, and eject families from shelter if they fail to hold up their ends of their "housing stabilization plans."

The mayor describes his strategies as attempts to motivate the homeless and near-homeless into self-sufficiency, and points out that his administration has successfully transitioned more than 210,000 individuals into permanent housing. Many activists criticize the Bloomberg innovations, however, as cosmetic or unnecessarily punitive quick-fixes that direct resources away from those who need them most.

Now, with sky-high unemployment rates looking like they're here to stay for months or years, and Bloomberg preparing for a third term in office, the number of people using the New York shelter system has hit record highs. Last month, the Coalition for the Homeless reported that over 39,000 individuals—including more than 16,000 children—were sleeping in city shelters each night. Last fiscal year, 45 percent more people slept in shelters than when Bloomberg first took office.

For this "virtual" conversation, City Limits asked a group of experts, from both the city government and the advocacy community, to respond via email to a list of questions about the current homelessness crisis, how the city got here and how New York can best move forward. Our questions and their answers are below.

The participants are:

Robert V. Hess, commissioner of the New York City Department of Homeless Services (DHS)

Laurence Belinsky, president and CEO, HELP USA, a service provider that contracts with the city

Matthew Wing, communications director for City Councilman, Council General Welfare Committee Chairman and Public Advocate-elect Bill de Blasio

Patrick Markee, senior policy analyst, Coalition for the Homeless

Rob Robinson, member, Picture the Homeless, and consumer co-chair, New York City Coalition on the Continuum of Care