5 Hard Lessons I Learned in My First Years as a Landlord

Quick Summary:

• You don’t know what you don’t know (and it’ll cost you).

• One property is fragile—scale brings stability.

• Most property managers aren’t great unless you stay on them.

• Look at way more deals than you think you need to.

• Bad deals don’t become good just because you want them to.

1. You Don’t Know What You Don’t Know

When I started investing in rental properties, I thought I was prepared. I read the books. I watched all the videos. I talked to other investors. I figured that would cover 80–90% of what I needed.

It didn’t.

There were so many things I didn’t even know I didn’t know—city rules, licensing laws, tenant expectations, and how hard it is to line up contractors when someone’s living in the property. Every week brought a surprise. And every surprise cost money.

It felt like I was walking through a maze blindfolded. I had a roadmap, but the map didn’t show all the traps, turns, and sudden drops.

Tangible Advice: Expect that you’ll miss things—and budget for it. Keep 3–6 months of expenses in reserve for each property. And when something goes wrong, don’t panic. That’s normal. Fix it, learn from it, and keep moving.

2. Scale Is a Lifesaver (Eventually)

In my first year, I had one or two rentals. When something broke—a garage door opener, a water heater—it wiped out all my profit for the month. I felt like I was running a business, but it didn’t feel like I was winning.

Now I’ve got 18 doors. When something breaks, it still hurts, but the other properties help cover it. It’s not a crisis anymore. That’s the power of scale.

Getting there took time. But growing my portfolio made the entire business more stable. What once felt like a financial emergency now feels like a line item.

Tangible Advice: Start small, but plan for scale. Don’t rely on one or two properties to pay your bills. Think of them as the beginning of a system you’ll build over time.

3. Most Property Managers Are Not Great (Unless You Make Them Be)

At first, I assumed property managers were pros who’d take care of everything. In reality, most property managers work under real estate brokerages that don’t actually focus on property management. It’s usually a side hustle for them.

The people managing your properties are often underpaid and juggling hundreds of units. That means unless you’re watching closely, your property is probably getting the bare minimum.

Leaks go unnoticed. Repairs get delayed. Preventive maintenance doesn’t happen. Then suddenly, a $50 repair turns into a $5,000 disaster.

Tangible Advice: Hiring a manager doesn’t mean you stop managing. Scrutinize monthly statements. Ask questions. Set expectations. And follow up. The more attention you give your property manager, the better your property will be treated.

4. You Need to Look at Way More Deals

When I bought my first properties, I looked at 10 or 15 and thought I was doing real work. Now I know that’s barely scratching the surface.

Good deals are rare. Most properties on the market are overpriced or just plain bad. Sellers try to squeeze every dollar they can. If you want a deal that really works, you’ve got to look at a lot of options.

My early search process was like speed dating—too quick, too hopeful. I wanted every property to work, and I started massaging the numbers to make them look better than they were.

Tangible Advice: Run the numbers on 100–150 properties before you buy one. No exceptions. Don’t settle just because you’re tired of looking. That’s how people end up with bad properties.

5. Don’t Fudge the Numbers

This one’s a killer. I used to say, “Maybe the rent will be higher than I think,” or “Maybe the repairs won’t cost as much.” I wanted the deal to work, so I tweaked the numbers until it looked good.

But that doesn’t change reality. If the numbers only work when everything goes perfectly, then the deal doesn’t really work.

Tangible Advice: Be honest with your numbers. Use conservative estimates for rent, expenses, and repairs. If the deal still works with worst-case assumptions, that’s a sign you’ve got something worth doing.

Final Thought: Stumble Forward

Real estate will test you. It’ll confuse you. It’ll frustrate you. But if you keep learning, keep showing up, and stay honest with yourself, you’ll grow into it.

Every mistake I made became a lesson that helped me do better the next time. Every stumble was just a setup for a stronger stride forward.