Not everyone's convinced the state's new "Return to Home" program will work.
"That's a lady, this is Al, that's Felix up there, another guy," explained Don "Action" Jackson, pointing to a row of tents and tarps in Kaka'ako where homeless people live.
Jackson told KITV reporter Lara Yamada he's been homeless, hanging out around there for nearly six years, and has no intention of moving.
"If I can't be here, I'd go over there, or across the street, or back over there," he said, pointing in different directions.
But with some 17,000 homeless people now living on Hawaii streets, lawmakers are getting desperate for solutions.
For the first time, a controversial new pilot program called "Return to Home" netted the money and support for a drastic approach this legislative session: $100,000 a year, for three years, to buy plane tickets to send the homeless -- home.
"It's kind of frustrating that I work 40 hours a week, and to send somebody back, well, I wanna go home, too," said Danielle Bourlier.
"Statistically, 20 to 30 percent of Hawaii's homeless population migrated to the islands recently, within the last two to three years, and for a lot of them, their dreams didn't materialize and they're caught within our islands wanting to go back home," said Rep. Rida Cabanilla by Skype from Las Vegas.
Lawmakers estimate it will cost taxpayers about $500 a pop to send people elsewhere, but argue it will cost taxpayers even more to keep them here anyway.
"Every homeless person gets a minimum of $700 a month in cash assistance or food stamps. They get that automatically," she said.
But the Department of Human Services predicts the program will be "...costly and administratively burdensome...," adding the state will also have to pay for identification, background checks, transportation and hygiene for a program not everyone's convinced will help.
"We've kicked people off beaches, off parks, recently we kicked them off sidewalks," said Tom Gill.
"A ticket to wherever. Unless they have some goals, you're just sending them to another state with the same problems they had out here," said Jackson.
Cabanilla said the voluntary program should start within the next three months -- where participants must have a designated person on the mainland picking them up.
Despite big reservations by state agencies and other organizations, she said in 2012 the state spent $63 million on Hawaii's homeless, and believes the program is worth a shot.