Flipping houses out-of-state

+ Dealing with squatters...

Author

Pablo Ottenwalder
December 05, 2025

Words I like: The only way to win in an unfair world isn’t to beg for fairness it’s to become so useful, so strategic, and so dangerous that no one can afford to ignore you.

Pablo’s Perspective:

This week I had one of the most out of state investor moments you can have -
my electrician called me and said:

“Someone’s inside your property.”

Now… when you’re flipping a house down the street, that’s annoying.
When you’re flipping 1,423 miles away, it hits different.

If you know Mass, you know it’s one of the most tenant-friendly (aka squatter-friendly) states in the country.
I’ve already spent $9,000 evicting one before…

Here’s what went down:

Someone Broke In…

My electrician found:

  • A mattress

  • Clothes

  • Blankets

  • Trash bags

Basically, someone setting up their own air bnb…

The Twist: NOT a Squatter

In Mass, to be a legal squatter you need:

  • Utilities under your name

  • Mail delivered

  • A fake lease / “proof” of residency

This guy was only there one day.
No utilities. No mail. No nothing.

So this wasn’t squatting.
This was trespassing and that saves me thousands.

What I Did (FAST)

  1. Documented everything.

  2. Got a locksmith + changed all locks.

  3. Boarded up the door he kicked in.

  4. Filed a police report.

  5. Installed cameras (lesson learned).

If you don’t move fast in Massachusetts, a trespasser becomes a tenant… and you’re screwed.

And after all this?


I’m gonna keep it real with you…

I’m done doing big out-of-state projects.
The stress, the laws, the surprises it’s not worth losing hair over a flip I can’t even drive to.

From now on, it’s cosmetic, light-touch, quick-in-and-out deals only.

Simple projects.
Tight timelines.
Cleaner profits.

That’s the new play.

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Book i’m currently reading - Meditations: A New Translation Marcus Aurelius

Did you know? 💡 

In the 1800s, over half of the U.S. was settled by squatters, not legal landowners.
People would move onto empty land, build a cabin, start farming, and dare the government to stop them.

Eventually the government gave up and passed the Preemption Act of 1841, which basically said:

“If you already squatted here, just pay a small fee and you own it.”

Millions of acres were legalized this way.

So yeah… a big chunk of America was built by the OG squatters.

-Pablo