Each year, cities all over the U.S. conduct a one-day count of homeless people, part of a federal requirement for cities receiving Continuum of Care funding from the U.S. Department of Housing and Urban Development (HUD). The last count was in January of this year.
The National Alliance to End Homelessness has created a nice Google map showing reports of homeless counts in a large number of cities, based mostly on reports in newspapers and other media sources in these local areas. On the map, red markers indicate media reports of increases in the number of homeless people, with green indicating decreases and yellow a mix of the two (increases in some sub populations and decreases in others).
Visually, red is "winning" on the national map, which may indicate that more cities are reporting increases in the homeless count vs. last year. There is undoubtedly other data consolidations elsewhere, but this is a nice visual representation.