On a Thursday night, Councillor is bustling with staff and servers doling out cocktails and pub fare.

But while the year-old upscale Parkdale sports bar is now thriving, it's owner says getting to this point was "hell," thanks to a cumbersome approval process at the city.

It took Chris Sherwood two years to actually open the bar on Queen Street West thanks to layers of red tape, including thousands of dollars for application fees and site maps, and trips to the committee of adjustment to get the green light for zoning variances.

Once Councillor opened, there was another challenge: getting people in the front door.

"It's a busy area, but the people who live the condos — they don't come out as often as people think they do," Sherwood said with a laugh.

Sherwood makes it all work through advertising and word-of-mouth promotion, but he's among those wondering if there's more the city could do to help support late-night businesses like his.

"We're supposed to be a world-class city," he said. "That's what world-class cities do."

Increasingly, Toronto's late-night scene is indeed on the radar of city officials.

On Wednesday, Mayor John Tory announced the appointment of Deputy Mayor Michael Thompson as the city's new "night economy ambassador." It's just the latest step to boost Toronto's overnight social and economic spheres following council's July endorsement of a report focused on strengthening the city's nightlife.

"Right now, the city is not set up to encourage [late-night] enterprises ... I think we have to take a look at the laws, regulations and practices," Tory said on Wednesday.

Businesses want fewer restrictions, lower property taxes

The growing focus comes amid fears over sky-high property taxes for corporate buildings — which are shuttering businesses like restaurants on main streets across the city — and a rising number of music venues closing down in recent years.

"We're losing venues now because they're being used for other types of economic initiatives and so on. This is an area we want to focus ... We are a music city," said Thompson.

Back at Councillor, Sherwood said the city could help businesses like his thrive by lobbying the province for lower commercial property taxes, which have been spiking thanks to rising building value assessments, and later drinking hours.

The province is reviewing its assessment system, officials recently told CBC Toronto, and already extended drinking hours to allow customers to imbibe earlier in the morning.

Ben Swirsky, co-founder of live music bar and restaurant Alchemy Food & Drink on College Street, agrees extending last call could be a boon for music venues in particular, which often rely on both foot traffic and, mostly, residents flowing in from other neighbourhoods.

"Obviously, you hope to be the next viral thing ... The reality is, it's more of a slow grind," he said.

To Sherwood, the top thing municipal officials need to look at is streamlining the approval process to get late-night offerings open in the first place.

"No one at city hall will actually leave their office and come inspect what you're trying to do," he said. "They just look at paperwork and say, 'Next, next, next.' It was long and tedious."

Ultimately, he said, Toronto needs fewer restrictions on where people can open late-night venues — since they're what keep neighbourhoods thriving around-the-clock.

"Restaurants, bars, cafes — they bring people together," he said.