The Man Named Lucky Whose Condo Board Seat Became a Financial Nightmare

Glen Fortunato sits in the courtyard of his North Park condo complex on a January afternoon, laptop balanced on his knees, toggling between a spreadsheet titled "Financial Apocalypse Scenarios" and a Slack channel where his freelance clients are asking about project timelines. He's 36, a brand designer who bought his first property here in July 2023. A one-bedroom unit he thought represented his entry into adult financial stability.

Eighteen months later, he's on the HOA board dealing with a $440,000 repair bill from mandatory balcony inspections, insurance premiums that have tripled, and neighbors who alternate between panic and rage in the building's group chat.

His last name, Fortunato, has become a running joke. "My family's from Sicily," he says, pulling up the inspection report on his phone. "The name means 'lucky one.' Real fucking prescient, right?"

The complex is a 1987 build. Sixteen units, Spanish-style stucco, with those classic San Diego wooden balconies that looked charming in the listing photos. The January 1st inspection deadline under SB 326 came and went, revealing dry rot in eleven of the sixteen balconies, waterproofing failures in nine, and structural issues in four that the inspector classified as "immediate safety hazards."¹ The building lost its liability protection on January 2nd. Glen became the board member tasked with figuring out what happens next.

You bought in 2023. That's catastrophically bad timing.

Glen: Oh, you noticed? Yeah. My friends kept saying I was getting priced out forever, that San Diego real estate only goes up, that renting was throwing money away. I had some savings from a good contract year, my parents helped with the down payment, and I thought, okay, this is what adults do. You buy property. You build equity. You make the smart long-term investment.

He laughs, but there's no humor in it.

The inspection was four months ago. We got the results in October. I've spent the last three months learning more about construction financing, insurance underwriting, and California HOA law than I ever wanted to know. I'm a brand designer. I make logos and motion graphics for tech startups. I don't know anything about load-bearing structures or reinsurance markets. I shouldn't need to know about reinsurance markets.

What is the board actually facing right now?

Glen: Okay. So. The repairs are $440,000. Our reserve fund has $62,000. We have sixteen units. That's a special assessment of about $23,600 per unit if we don't finance it.

Most people can't write a check for $24k. Hell, I can't write a check for $24k. So we're looking at taking out a loan.

But here's where it gets fun. Our building insurance was $18,000 a year in 2023. Renewal came up in December, and the quote was $54,000. Triple. The insurance company said they won't renew at all unless we complete the balcony repairs by March.²

So we need the loan to do the repairs to keep the insurance to maintain the property values that are currently cratering because everyone knows we're about to hit owners with a massive assessment. It's like a financial Rube Goldberg machine designed by someone who hates me personally.

We got quotes from three lenders. Best rate is 8.2% on a ten-year note. That's about $5,400 per month in debt service, which means HOA fees go from $280 a month to around $620. Plus the insurance increase. We're looking at $750 to $800 monthly HOA fees by summer.

Have you told the other owners?

Glen: We had a meeting last week. Zoom, because half the board didn't want to do it in person. I presented the numbers. There was this very long silence where I could see people's faces on the screen just... processing. And then someone asked if we could just not do the repairs. Like, just accept the risk and skip the whole thing.

I had to explain that we already lost our liability protection. If a balcony collapses and someone gets hurt, we're personally liable. The board members, I mean. That got people's attention.

Then someone else suggested we sue the inspector for finding too many problems. I'm not joking. They wanted to sue the inspector for doing the inspection the state required us to do. I muted myself and screamed into a pillow.

The meeting ended with about half the owners saying they'd just sell, and the other half asking if we could delay everything until after summer because they didn't want this affecting tourist rental income. We have a second meeting scheduled for next week. I'm drinking heavily in preparation.

What does your unit look like on the market right now?

Glen: I bought for $385,000 in 2023. Zillow currently estimates it at $340,000, but that's before the special assessment news is public. My realtor friend said once the assessment hits public records, I'm looking at maybe $290,000 to $310,000.

He pulls up a spreadsheet, scrolls through it without really looking.

So I'm underwater by at least $75,000, probably more like $95,000 when you factor in what I've paid down on the mortgage. If I sell now, I take a massive loss and still owe money. If I stay, my housing costs jump by $500 a month and I'm locked into a building where half my neighbors are trying to flee.

The people who do stay will be the ones who can't afford to leave, which means future assessments get harder because the financial burden concentrates on fewer solvent owners. It's like musical chairs except the music is the sound of property values collapsing and there aren't enough chairs.

You mentioned tourist rentals?

Glen: Oh yeah. Four units are full-time short-term rentals. Which is its own problem because those owners don't live here and vote against anything that costs money. One of them lives in Phoenix. Moved there last year, kept the condo as an investment property. He's the most vocal about not doing the repairs. Says we should just get cheaper insurance.

I tried to explain that cheaper insurance doesn't exist. We're in California. We're near the coast. We have wooden balconies with dry rot. The only option cheaper than $54,000 is the FAIR Plan, which would be about $70,000 and covers less.³ He told me I wasn't being creative enough.

What would creative look like?

Glen: Laughs I don't know, man. Sacrifice a goat to the insurance gods? Rebrand as a high-risk adventure housing experience? "Live dangerously in North Park. Balconies may or may not support your weight. Find out!"

I design brands for a living, and I can tell you there's no brand strategy for "your balcony might collapse but the HOA fees are reasonable."

The thing that keeps me up at night is that this isn't even climate change in the dramatic sense. We're not in a wildfire zone. We haven't flooded. This is just wood rot. Normal building maintenance that should have been done years ago but wasn't, and now the regulatory deadline forced everyone to confront it simultaneously while insurance markets are imploding for completely separate climate-related reasons.

Separate reasons?

Glen: The insurance increases aren't about our building specifically. They're about the entire California market. The reinsurers—the companies that insure insurance companies—got hammered by the LA fires, the Paradise fires, all of it. So they're raising rates across the board and pulling out of risky markets.⁴ We're just collateral damage.

Our balconies would need repairs regardless, but the insurance crisis makes it financially catastrophic instead of just expensive. It's like I thought I was buying into stability. A fixed asset, a place to live, a smart financial decision. And instead I bought into this cascading series of systems that are all failing at once for reasons that have nothing to do with me but everything to do with me.

He closes the laptop, then immediately reopens it to check something.

Sorry. I keep checking to see if the numbers have changed. They haven't changed.

Are you going to stay?

Glen: I genuinely don't know. Every spreadsheet I build shows a different answer. If I sell now, I lose $95,000 but I'm free. If I stay and the building stabilizes, maybe I recover some value in five years. If I stay and more owners bail, I'm trapped in a death spiral of rising assessments and falling values.

My parents keep asking what I'm going to do. They helped with the down payment. They feel responsible. I keep telling them it's not their fault, but also... they gave me money to buy into a system that's actively collapsing. That's hard to process. For both of us.

What do your friends say?

Glen: The ones who rent are very smug. The ones who bought houses in less climate-risky areas are sympathetic but clearly relieved it's not them. I have one friend who bought a condo in Florida in 2022, and we have these very dark text exchanges about who made the worse decision. He's dealing with hurricane insurance. I'm dealing with balcony rot. We're both dealing with the reality that "building equity" might have been a trap.

The worst part is the advice everyone gives. "You should have gotten a home inspection." I did get a home inspection. "You should have reviewed the HOA finances." I did review the HOA finances. They looked fine. The reserve study from 2021 said we were adequately funded.

Nobody mentioned that the reserve study was based on 2019 construction costs and 2018 insurance rates. Nobody mentioned that the entire insurance market was about to implode. Nobody mentioned that buying property in 2023 was like buying a ticket on the Titanic in 1912 because the ship looked really nice.

What happens at next week's meeting?

Glen: We vote on whether to take the loan. If it passes, we move forward with repairs and accept the fee increases. If it fails, we're in some kind of legal limbo where we're required to do repairs we can't afford, which probably means the building goes into receivership or something. I've been reading HOA law forums at 2 AM trying to understand what happens when an entire building just can't.

I'm voting yes on the loan because the alternative seems worse, but I'm not confident we'll get enough votes. People are angry. They want someone to blame. Some of them blame the inspector. Some blame the previous board. Some blame climate change, which at least has the virtue of being accurate but doesn't help with the immediate problem.

There's this one guy who keeps posting in the group chat about how this is all a conspiracy by insurance companies to drive up profits. And like, I get the anger, but also we have actual dry rot. The balconies are actually failing. The conspiracy is just capitalism plus climate change plus deferred maintenance, which is somehow both more mundane and more terrifying than a conspiracy.

Do you wish you'd stayed renting?

Glen: Every single day. I'd be paying $2,200 for a one-bedroom right now instead of $2,100 for a mortgage plus $280 in HOA fees that's about to become $800. I'd have flexibility. I could leave. I wouldn't be on a board trying to explain to my neighbors why we can't just ignore structural engineering.

But also, renting felt like failure. Like I was thirty-five and still not a real adult. Buying felt like I'd finally done the responsible thing.

“

"And now the responsible thing is bankrupting me while the irresponsible thing would have left me solvent and mobile."

I don't know what the lesson is. Don't buy property? Only buy property in climate-safe areas, which don't exist? Accept that long-term financial planning is impossible when the systems we built those plans around are disintegrating?

My parents bought their house in 1987 for $140,000. It's worth $1.2 million now. They keep telling me real estate always recovers, just wait it out. And I'm like, yeah, but did your HOA fees ever triple in six months? Did your insurance company ever threaten to drop you because of climate risk? The rules changed and nobody told us.

What's the best-case scenario?

Glen: We pass the loan, complete the repairs, insurance stabilizes at the higher rate, and in three to five years the market recovers enough that I can sell without catastrophic loss. I eat the higher HOA fees, I stay put, I treat this as an expensive lesson in reading the fine print of civilization collapse.

Worst case? The loan vote fails, the building enters some kind of legal crisis, my unit becomes unsellable, and I'm stuck paying a mortgage on a property I can't live in safely and can't sell. Or the loan passes but more owners bail, the assessment burden concentrates, fees spiral higher, and we end up in the same place just more slowly.

Medium case? I sell now, take the loss, move back to renting, and spend the next decade rebuilding savings while watching everyone else who bought property deal with versions of this same crisis in slow motion.

He closes his laptop again, keeps it closed this time.

I'm supposed to send the board my recommendation by Friday. Right now my recommendation is "I don't know, and anyone who claims they do is lying." But I don't think that's what they want to hear.

What they want to hear is that there's a solution. That someone smarter than us can fix this. That the spreadsheet has an answer if we just format it correctly. But the spreadsheet doesn't have an answer. The spreadsheet just has different versions of expensive and bad.

I keep thinking about my last name. Fortunato. The lucky one. My grandfather survived World War II, came to America with nothing, built a life. My parents bought a house that made them millionaires just by existing. And I bought a condo with balconies that are rotting off the building while insurance markets collapse.

The luck ran out somewhere between their generation and mine. I just didn't know it yet when I signed the papers.