On a single frigid night in late January, roughly 20 Milwaukee County outreach workers fanned out across the county in five teams, cruising to known sleeping spots and checking dark corners most residents never see. They offered shelter, sandwiches and quick surveys to people sleeping outside. The county’s annual Point-In-Time count, a one-night snapshot, is the main federal benchmark for tracking local homelessness. But because it only measures who is in shelters or literally sleeping in places not meant for human habitation, many people bouncing between couches, motels or unsafe housing never show up in the numbers.
The Point-In-Time count is a federal requirement. HUD directs Continuums of Care to carry out sheltered and unsheltered counts on one night in the last ten days of January, as laid out in HUD's methodology guide. Auditors and researchers have long warned that the method can undercount hard-to-find groups and have recommended stronger guidance and better use of data from other systems, according to the Government Accountability Office. That context helps explain why many counties now pair the one-night count with year-round records and follow-up outreach.
For the people doing the work, the night is part census, part human contact. Outreach teams drove assigned routes, checked familiar encampments, offered rides to shelter and documented each encounter, as reported by WUWM. Milwaukee County’s Eric Collins-Dyke summed up the balancing act: “We’re out here to gather information and data, but we’re also trying to convince people to come inside.” Nancy Esteves of HMIS added a memorable comparison: “Point-In-Time is the snapshot, HMIS is the movie.” Those paired tools help planners decide where limited dollars should go.
Local declines tied to a Housing-First approach
In that imperfect framework, Milwaukee’s recent numbers still stand out. County officials reported only 17 people counted as unsheltered on the night of the most recent tally, a record low for Milwaukee County, according to a Milwaukee County press release. Local leaders and funders credit a Housing-First approach, which focuses on moving people into housing quickly and then layering on services and supports. The United Way’s Safe & Stable Homes initiative has pointed to that strategy as a key driver of recent declines. At the same time, advocates warn that those gains depend on stable federal funding and predictable grant rules, neither of which feels guaranteed right now.
Federal rule changes cloud local gains
Recent decisions in Washington have thrown a wrench into that progress. A controversial FY2025 Continuum-of-Care notice would have capped permanent-housing funding at roughly 30% of a CoC’s annual renewal demand and shifted priorities toward transitional or service-tied projects, a move that sparked lawsuits and urgent objections, as reported by Politico. In response, HUD temporarily withdrew that notice and said it would reissue a modified NOFO while it reviews the legal challenges, according to HUD’s CoC updates. The sudden shift forced many local Continuums of Care to pause or rewrite their competitions while providers wait to see what the final rules look like.
What this means for providers
Service leaders say the real-world impact is felt in cash flow, not acronyms. United Way impact manager Krystina Kohler told WUWM that providers could see a funding gap of several months even if awards are eventually reissued. Some agencies may have to lean on private lines of credit just to keep staff paid while federal rules get sorted out. That kind of strain hits small nonprofits hardest, especially those that run outreach, case management and permanent supportive housing programs.
For now, outreach teams will keep knocking on tent flaps, car windows and shelter doors, trying to build trust one conversation at a time. Local leaders say the next few weeks and months, as HUD and the courts hammer out FY2025 funding rules, will decide whether Milwaukee can hang on to the Housing-First gains that helped drive unsheltered counts to record lows, or whether that progress ends up being just another one-night snapshot.
