Wyarunga man Craig Chamberlain has been living in a hotel near Barangaroo for the last month. On Friday, May 29, he found out his stay is extended for another 30 days.
When the pandemic struck he was living in Matthew-Talbot hostel, a homeless shelter in Kings Cross.
"We were all worried that we'd get infected with the COVID and we'd either be isolated or kicked back out onto the street," Mr Chamberlain told NITV News.
"But when we found out they were going to put us in hotels, the fear and stress went away, and some hope came back."
For the time being, Mr Chamberlain is waiting to receive a payout from his former employer before retiring somewhere outside of the city.
Across town in the Crowne Plaza on Coogee Beach, former rough sleeper Benjamin Valentine also received some good news.
He has been meeting weekly with the community organisation Neami to address any of his health, mental health and housing needs.
"I've just been offered a place in supported accommodation; it's the next step towards housing," Mr Valentine told NITV News.
"There has been a lot of progress and benefits from the program that's been put forward by the government."
Neami received $3 million from the NSW government to work closely in assisting with housing rough sleepers during the pandemic.
The organisation's Indigenous liaison officer and Wiradjuri man Trent Kilby said the benefits he's seen for Indigenous people in the program has been significant.
"I was sitting with a gentleman about a week ago, and even though he did transition into stable accommodation, I think he enjoyed the fact that he could sit there and share his story," Mr Kilby told NITV News.
"He was a proud Aboriginal man, and just having someone who could sit across from him was good."
Neami regional Manager, Shane Jakupec, said that some people have found it hard adjusting to living in a small room after so much time spent out on the streets.
He added that with restrictions easing, some people have a sense of security and confidence to go "back out onto the streets."
"However, the vast majority of people have found the hotels to be a useful and safe place."