‘Meet the Activist Who Hunts for San Diego’s Airbnb ‘Apartment Hotels’

by Cody Dulaney / inewsource /  September 23, 2026

Jay Goldberg swears he’s a capitalist.

It’s a Thursday afternoon and the 42-year-old Hillcrest homeowner is seated at his kitchen counter, scrolling through lines of code he wrote to analyze multiple datasets on his laptop. He’s a Google engineer by trade, but his workday is over, and now he’s hunting through the local real estate market.

His target? Properties that he calls “apartment hotels” — or entire complexes that have been converted from long-term housing to short-term rentals.

He’s a capitalist, he says, but he’s a capitalist with guardrails, driven by one guiding principle: What’s good for one person shouldn’t come at everyone else’s expense. And he’s become convinced that’s exactly what’s happening in San Diego.

Earlier this year, inewsource revealed a glaring loophole in a San Diego law that allows property owners to obtain a short-term rental license even after carrying out an illegal eviction. It works like this: Investors buy up multi-family properties, clear out the long-term tenants with buyouts or no-fault evictions, and post the units on short-term platforms, such as Airbnb.

Goldberg has spent years working to identify these properties.

He gathers data from short-term rental platforms. He combs through active licenses and property records. And when he thinks he’s identified an apartment hotel, or really any short-term rental violation, he turns over what he finds to San Diego officials.

Then he waits.

Goldberg has developed a system — so much so that, by his count, he and a small group of others have filed more than 2,000 reports with the city of San Diego, flagging everything from improper signage and illegal garage conversions to hot plates spotted in listing photos.

Their campaign has turned Goldberg and his allies into citizen activists, pushing the city to enforce its own laws and creating a paper trail that, if nothing else, makes it hard to ignore properties they believe are skirting the rules.

“The reason I’ve filed 2,500 reports is not because I expect them all to be solved in a reasonable amount of time or that I even personally think they should all be prioritized,” Goldberg said. “But they’re flags in the sand that say something happened. There’s something that happened here at this time and you can’t sweep it under the rug.”

Goldberg’s interest in short-term rentals started close to home — as a neighbor. A dispute over the townhouse next door, which was operating as a full-time vacation rental, led him to start looking beyond his own shared wall.

Goldberg later founded Nice Neighbors, a data-driven citizen watchdog group that advocates for “common-sense Airbnb regulation” and enforcement.

The website includes an interactive map of short-term rentals and a repository of active licenses, Airbnb listings, as well as conversions of apartments to short-term rentals, among others. There are multiple ways for people to report a concern about a short-term rental through the website, either with Nice Neighbors or directly with the city.

“I want people to seek justice,” he said. “I actually want them to be angry, because anger is what motivates people. Personal discomfort is where change is born. And I think there’s a lot of personal discomfort that everyone is suffering in their own silos.”

San Diego leaders have for years grappled with two competing realities: a worsening housing and affordability crisis coupled with the business interests of property owners in a world-class destination city.

Experts largely point to a fundamental shortage of housing, built up over decades of failing to produce enough homes for residents of all income levels. Half of the city’s current housing supply consists of rental units that are nearly full, which keeps rents high.

Goldberg and his allies see another force driving the affordability crisis, though. Without stronger regulation and enforcement, they say, property owners are incentivized to turn long-term housing into more profitable short-term rentals.

Every other major California city has rules in place to prevent investors from flipping housing stock to full-time vacation rentals, said Cynara Velazquez, one of several Ocean Beach residents who teamed up with Goldberg. Velazquez is a consultant who co-founded a political action committee called Housing for San Diegans. The PAC promotes candidates who have pledged to limit Airbnb and, conversely, alerts voters to candidates backed by the platform.

Velazquez said Goldberg has organically attracted a following of several concerned residents in Ocean Beach, where folks are apparently dealing with a high concentration of these apartment hotels selling beach access and sunset views to tourists from units that were once naturally affordable.

And it’s disrupting the housing market, Velazquez said.

“We’re fighting an uphill battle against a multinational corporation with unlimited money to spend in San Diego, securing the vote of San Diego politicians,” she said. “Thank goodness there are people like Jay who have so much talent and have made this their hobby.”

Response from San Diego officials
Several members of city staff, including the department charged with regulating short-term rentals in San Diego, declined to comment on this story. For context, a spokesperson said more than 4,400 reports have been filed since 2024.

Goldberg says he has had success, crediting himself for helping to identify and ultimately shut down at least a dozen “bad actor hosts” who are no longer allowed to run short-term rentals in San Diego.

“I think I’m a little obsessed with power imbalances, I’ll admit that, and there’s a lot of power imbalances,” he said. “Someone who has enough money to buy a multi-family building, do all the renovation and eviction to turn it into an Airbnb, has several other Airbnbs … how are you, as a tenant, equipped to deal with that kind of power?”

Michael Flore said the phone call came out of nowhere.

He had just moved out of a two-bedroom Pacific Beach apartment that he had rented for more than a decade. One block from work and from the Catamaran Resort, his rent was just $625 when he signed the lease in 2009 — and it hadn’t changed much over the years.

So when new owners bought the apartment complex and offered each tenant money to leave in 2023, Flore wasn’t sure what to do. But they were “very persistent,” he said. When he didn’t accept the offer right away, a real estate agent hired by the new owners knocked on his door.

They will find a reason to kick you out, Flore remembers the agent telling him. You might as well take the money.

“I thought I had no other option,” Flore said. “As soon as we came to some kind of agreement, I found out that I did have options.”

Flore scrambled to learn more about those options, researching tenant protections and housing law and reaching out to anyone he thought might be able to help. But the clock was ticking. Eventually, it was time to leave.

“Since I had been in my place for 15 years, I couldn’t find anything even close to what I had, so I had to move back to New York,” he said. “I had two bedrooms’ worth of stuff I had to get rid of in three weeks. I had to throw out basically most of my life. I ended up just taking a bag back to New York.”

Not long after he left, his phone rang.

Goldberg was on the other end.

His data analysis had flagged Flore’s building as a possible “apartment hotel” conversion. Goldberg looks for a number of indicators, including how many short-term licenses are obtained after a property changes hands. When more than half of the units in a multi-family development have licenses soon after the sale, he starts making phone calls.

Goldberg found Flore’s number through a public records search. He wanted to hear what happened, he told Flore, and see whether he could help shine a light on his experience.

“Jay came out of nowhere,” Flore said. “I was just finally like, ‘Oh, somebody does care about what’s going on.’”

For Flore, though, the call came too late. He had already moved out.

“How everything happened, it was so quick,” Flore said. “I felt a little bummed at first for myself, wishing I knew of Jay right when this was happening to me, but obviously the situation is a lot larger than just myself.”

“I think what Jay is doing is amazing for sure,” he added.