Decrepit water and sewerage pipes, a spike in crime in the city centre, bickering councillors, empty old buildings. The "coolest little capital" is weighed down by some big problems.
"There are a lot of infrastructure problems that are sapping some of Wellington's mojo," Dominion Post editor, Anna Fifield says.
But that's just the beginning. Today The Detail looks at what's wrong with Wellington and what it will take to get back its magic charm.
Fifield talks to Sharon Brettkelly about her impressions of the city she calls her spiritual home in New Zealand after 20 years overseas, and to City Councillor Nicola Young about the challenges of fixing the problems.
Ask any Wellingtonian what they love about the city and they say it’s the people.
"The people are lovely," a dairy owner tells The Detail. "Different, quirky, although we might dress in black we've got Cuba Street, we've got zany characters, the politicians, all the bureaucrats, all the suits. We've got an eclectic mix of people."
Some rave about the wind, others love the easy access to events around the city and the cafes that serve excellent coffee are endless.
"It’s just so rich, the life," Fifield says. "But it’s also extremely depressing to walk around the streets of Wellington and to see all of these buildings that are closed for earthquake strengthening. There's the civic square buildings which are closed but then you also have the Reading Cinema, like this big, hulking shell on Courtenay Place; the Amora Hotel, all these private buildings as well which are just sitting there."
Add to that a much quieter CBD as more people work from home, "sewage running through the streets" and a dysfunctional group of city councillors.
Fifield is also critical of the council's lack of vision for the city as it grapples with the massive earthquake strengthening bills for the public buildings and the task of fixing the infrastructure.
She relates her own experience of buying a house and the closed tender system that she believes exacerbates the problem of soaring prices.
Fifield wants the city's residents and leaders to have a wider discussion about the causes of the inner city crime and the lack of services for people living on the streets or in emergency accommodation.
But tackling the city's social problems and the housing crisis are too big for the council, Nicola Young says. It needs help from central government, she says.
"This is beyond the ability of the council to deal with. We're trying to get the pipes organised. Yes we have a role in housing but this sort of stuff is beyond our remit really."
Young says she is proud of the work the council is doing to restore several of the major buildings. The town hall will be completed in 2023, the St James Theatre will open in time for the International Arts Festival next year and the convention centre comes on stream in 2022.
"It’s not all doom and gloom," Young says.