And the gruff-looking man, who was once known to many as "Brutus" for his physical resemblance to the Popeye character, has made many friends in the neighbourhood.
Those friends included former City of Vancouver homeless advocate Judy Graves and Pastor Bob Swann of First Baptist Church.
But despite their best efforts, they were never able to help Jim find a suitable room of his own.
"Between living outside and some of these hotel rooms, I will sleep outside," says Heiberg.
But he admits years of sleeping out have taken their toll.
"I would love to get inside...I'm almost 60 years old, and I've been outside too long."
Judy Graves first met Heiberg in her own back alley, 14 years ago.
"He was much healthier, much stronger," says Graves, who retired in last year.
She remained determined to find housing for her friend on her own time, because she feared he would not survive outside much longer.
Miracles do happen
But Heiberg's options are limited. Most of the rooms available to him are in a neighbourhood that he desperately wants to avoid.
"Jim can't survive in the Downtown Eastside," says Graves.
"He's just got a complex set of disabilities that don't work down there."
As a result Heiberg has been on waitlists for the limited housing options available to him, but never selected.
Then on March 14, with help from Graves, that all changed when he found housing at Granville Residence, a city-run former SRO near the Granville Bridge.
"It took a bunch of miracles," says Graves, who managed to contact the building at the time a rare room came up.
Because there are far more homeless people than there are rooms available, she compares finding a home to a high stakes game of musical chairs.
It takes a village to keep a home
And once someone is inside, it can take a village to keep that person there.
Bob Marwick with the First Baptist Church Shelter Program says there's more to getting someone off the street than just finding a room.
It takes engagement from people like public health nurses and outreach workers. It's something Marwick is seeing more of in the city.
"They really follow through seeing how the residents are," says Marwick.
"I think that's what's needed, rather than just putting people in a room who have lived years on the street in room and they have to relearn the skills to live indoors, after being outdoors for many years."
Bob plans to check in with Heiberg at least once a week to make sure things run smoothly.
As for Heiberg, he is settling into his small but clean room, complete with his own bathroom.
"I never expected I would have a room like this, says Heiberg, who says it beats his little cubbyhole in the back alley.
"I am so happy," he says, as he gets ready to send his first night in his own home in years.