Why I Would Never Buy Rental Properties Again

Why I Would Never Buy Rental Properties Again

Buying rentals is not a good idea, especially if you're a tech person. Trust me, I've done it and I would NEVER do it again.

I bought 400+ rentals across the US, all-cash and 100% owned by me. I figured I would enjoy retirement, travel around the world and enjoy the cashflows.

WRONG.

Rentals are not passive investments. They are way too much stress. I could give you 100 reasons why owning a rental sucks but I'll just share 3.

Gut-Wrenching Decisions

I had to make the gut-wrenching decision to evict so many people who didn't pay rent. A passive investment should not require you to make decisions that impact people's lives.

And in places like San Francisco, it's another extreme where you have to give 'cash for keys' to professional squatters!

Drowning in Paperwork

I was drowning in paperwork constantly.

Management contracts, change orders, insurance certificates, escrow paperwork, easements, title documents, LLC resolutions. It felt like every week there was a mountain of paper that needed wet ink signatures and initials on all 100+ pages AND notarization!

Everything Breaks

Something is always breaking. Roofs. HVAC systems. Water heaters. Plumbing leaks. Foundation issues. Appliances. Eventually, my brain.

Thank god I hired property managers otherwise I would have to deal with tenants directly:

  • I'm locked out.
  • My toilet is clogged.
  • Change my lightbulb.
  • Next door has a pitbull.
  • Next door is also a meth lab.

My phone never stopped ringing.

Not Worth It

The financial returns are NOT worth the stress! If you're thinking about building wealth, consider how turning a bad startup into a major exit might be a better path. Or look into transforming a service into a scalable business instead of chasing rental income.

Passive income sounds great on paper. But rentals aren't passive. They're a second job that calls you at 2am about a burst pipe.

Think twice before buying that investment property.