Real Estate Investment Mistakes: What Did You Learn From Your Early Missteps?

Question

Hi everyone,

I'm reaching out to both beginner and experienced real estate investors to gather insights about common mistakes you made when you first started investing. We all know that mistakes are part of the learning process, but I’m curious to hear what specific challenges you faced early on and how those experiences shaped your approach going forward.

• What was the biggest mistake you made when you were just starting out?
• How did you overcome it, and what did you learn from it?
• Looking back, what would you do differently now that you have more experience?

For beginners, I’d love to hear about the hurdles you’re currently facing and any advice from seasoned investors on how to avoid those common pitfalls.

Looking forward to your stories and tips!

Thanks!

Ryan Spath · Answer

Great conversation! My biggest learning experience was not having an early termination clause in our leases. We had a tenant sign a lease and move in for a short period of time, they ended up purchasing a home and we had to re-rent the home in a month that is less ideal to have turnover. This cost both time and money, we now had to list the property for rent, screen tenants, move them in (at a lower rate).

We have since included a early termination clause in our leases that allows the tenant to buy out lease at a predetermined fee. This has made those conversations much easier when we are approached by current occupants that do want out of the lease early.

Haneef Porter · Answer

Yes, that’s something I’ve been afraid of because I know people that went through the same thing. But as me being a beginner those type of areas are more affordable as far as price for me to purchase 1st property. Any suggestions????

Jules Aton · Answer

I bought one I thought was just kind of ugly and outdated. After closing I discovered the wastepipe between house and sidewalk was broken which was expensive and there was frequent work necessary over the next few years. It was in a desirable area so remained occupied but was costly and a pain in the early days. Now that I have more capital I tend to replace things proactively before they actually break on Christmas eve at 11pm.

Dave Charron · Answer

I bought properties in bad areas of the city.  I spent more time with tenant issues, late rent or no rent than i did anything else.  They wreck the properties and are just terrible people to deal with.  Never made any money.  Only when i sold, cleared a little bit.  That was 20 years ago.

Now Ive got better properties, in better areas with better tenants and actually have cash flow!

Aaron Ameen · Answer

Hey Haneef, great question. Mistakes are inevitable, but learning from them quickly is what really matters.

Early on, my biggest mistake was not raising rent consistently. I left rent flat for three years, thinking I was keeping tenants happy. Meanwhile, the market moved up 60%, and I was way undercharging. When I finally adjusted, I lost a tenant, had to navigate turnover, and dealt with a much bigger headache than if I had just kept up with small, steady increases. Lesson learned: gradual adjustments are much easier than big jumps later.

Another big one? Not firing a bad property manager fast enough. Our first remote rental in Iowa seemed like a smooth deal—fully renovated, no major work needed. But within 45 days, our property was abandoned by the PM. Utilities were never turned on, pipes froze and burst, and they let prospective tenants show themselves through the house with no supervision. Meanwhile, the only time we heard from them was when they charged us for “snow removal” that we later confirmed never happened.

It was a disaster. But instead of pulling out of the market, we fired them immediately, brought in a great PM through a local agent referral, and had the home leased within a week. If I had cut ties sooner, I would have saved myself thousands in unnecessary damage and stress. Now, I don’t hesitate—if a PM stops communicating, delays rent, or mishandles maintenance, I fire fast and move on.

If you’re just starting out, focus on controlling what you can—good deals, good management, and keeping cash flow strong. If you want to chat more, I’ve got a full breakdown of my portfolio and lessons learned. Feel free to DM me—happy to share insights!