The Library of Congress site is indispensable for jive like this. These are all available at American Memory and some of the great stuff that makes paying taxes worthwhile http://memory.loc.gov/ammem/index.html . All of them were taken on Lower Douglas in Omaha by photographer John Vanchon. One of the photographs of Lower Douglas labeled Omaha "one of the great hobo centers of the West". Indeed these scenes likely aren't more than a block or four from where people now complain about the homeless hanging out around the front of the downtown Omaha library. Those two guys in the second photograph sure look up to something.
Of course, no mention of Lower Douglas could be made without mentioning Anna Wilson, one of Omaha's most well-known madames, whose brothel was donated for a hospital after her death, likely this one. If this was Anna Wilson's those newer looking wooden posts out front used to be nude women carved out of stone.