Vacancies, evictions, and unexpected costs: Real estate investors open up about the challenges of owning property

• Real estate investing can be a powerful wealth builder, but it comes with growing pains.
• Four investors share the top challenges they've faced, from vacancies to evictions.
• Still, they agree that the long-term upside outweighs the short-term strain.

Jeff White and Suleyka Bolaños bought their first investment property in 2017 to create an extra revenue stream and fast-track their early retirement goal.

Before their first rental property, a fourplex in Denver, generated a single dollar in income, it generated a string of problems, from cockroaches and mice to mold, squatters, and an eviction.

"It took us three months before we could fully move in," White said. "There were like eight people living there that we had no idea about. These people had been paying the previous owner cash, and they didn't even know the place had sold. It was a whole situation. That was our first eviction."

The couple had used owner-occupied financing to buy the property with a low down payment and planned to "house hack," or live in one unit while renting out the others. Instead, they spent months renovating, living in Bolaños' sister's basement while gutting units and dealing with pests and unexpected tenants.

"At the end of the day, it did end up working out for us, but it was definitely a really rough start," Bolaños said.

Nearly a decade later, the couple has reached financial independence by repeating their house hacking strategy: Buy a primary residence, rent out part of it for a year, then convert it to a full rental before moving on to the next property. They've added roughly one property a year to their portfolio since 2017.

Their rocky start underscores a reality many investors face: Rental income is rarely passive, especially in the beginning.

Vacancies can drain cash flow

Even investors who avoid nightmare tenants face another common challenge: vacancy.

Carolyn Yu, a 27-year-old accounting professional, is building a rental portfolio with the goal of eventually leaving her day job. She bought her first condo in late 2024 — "probably the worst time to rent because of winter vacancy," she said. It sat empty for six months.

To secure a tenant, she lowered the asking rent by about $100 a month. The prolonged vacancy was stressful, though manageable, because she paid for the property in cash and didn't have a mortgage. Still, she was responsible for about $600 a month in HOA dues. Plus, during the vacancy, mold developed, requiring professional remediation.

Her takeaway: expect the unexpected, and build a cash cushion.

"You have to know your numbers inside and out, so you're not guessing, and you have to expect surprise repairs because they will happen," Yu said. She recommends setting aside at least six months of expenses and taking time to build a trustworthy team. "Once you understand the risks, you can take action."

It's not as passive as it looks

For Stephen Yin, who owns multiple out-of-state rental properties, the workload comes in waves.

"By no means do I spend a consistent amount of time on my portfolio weekly," Yin said. Rather, it's more episodic. For example, when he's buying a property, the weeks leading up to closing can be intense — reviewing paperwork, coordinating inspections, and wiring funds — but between acquisitions, the workload may lighten.

Issues still pop up, sometimes at inconvenient times. Once, while on vacation, "I got a notice from my tenants about a woodpecker problem," Yin said. He called pest control, coordinated an inspection, and reviewed the report, all from abroad.

He uses the 80-20 rule to describe the effort required to maintain his portfolio: "20% of my houses take up 80% of my time." Some properties run smoothly, while others demand attention.

Being a landlord can be unpredictable and, at times, stressful. Vacancies eat into profits, while repairs can wipe out months of cash flow, and tenants don't always pay on time. But for investors like White, Bolaños, Yu, and Yin, the long-term upside outweighs the short-term strain.

White and Bolaños now say the difficult fourplex that once felt like a mistake became the foundation of their financial independence. Yu sees early setbacks as part of the learning process. And Yin, whose goal is to build generational wealth, views the challenges as part of the business.

"The stress is totally worth it," he said.