21 Times When Real Estate Investing Is Actually The Worst


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1. When you visit your rental property and realize your tenant is a hoarder.

Source: reddit.com

2. When the government passes new legislation that makes it harder for real estate investors to do business.

no cashflow
Source: ebaumsworld.com

3. When you’re walking through a foreclosure and the property is a significantly more disgusting than you were expecting.

Source: reddit.com

4. When you’re at an open house for a potential investment property, and you run into one of your competitors.

Source: ebaumsworld.com

5. When your CPA is trying to explain the benefits and tax implications of using a Self-Directed Roth IRA over a traditional 401K retirement plan.

Source: ebaumsworld.com

6. When you buy a property in a “War Zone” neighborhood, just because it was cheap.

Source: ReactionGIFs.us

7. When you visit your rental and discover that your tenants have trashed the place and moved out in the night… ย and you’re left to deal with the ensuing carnage.

Source: 4GIFs.com

8. How it feels when you hand the keys to your first rental house over to a property manager.

Source: ebaumsworld.com

9. When you’re trying to sell a property and someone offers you 50% of your asking price.

Source: ebaumsworld.com

10. When your variable rate mortgage starts ticking up with rising interest rates.

Source: ReactionGIFs.us

11. When you pay $30 for a real estate book, read it cover-to-cover, and realize you could have gotten the same information for free on BiggerPockets.

Source: 4GIFs.com

12. When you get home from working on a vacant rehab project and realize you forgot to lock the doors.

Source: ReactionGIFs.us

13. When you pull into your driveway and realize you forgot the ONE item that you just drove 45 minutes to get from Home Depot.

Home Depot
Source: ebaumsworld.com

14. When you ask your spouse to come along with you to visit some potential investment properties.

visit rentals
Source: ebaumsworld.com

15. When you’ve spent over a year trying to coach a rookie investor, and they buy a property with negative cash flow.

83400697Source: ReactionGIFs.us

16. One month after you buy a new duplex, and your property manager tells you both furnaces need to be replaced.

Source: ebaumsworld.com

17. When you’re walking through a foreclosure and you discover a homeless man living in the bathroom.

homeless man
Source: gifbin.com

18. Two weeks after you buy a new rental house, and your wife asks if it’s making any money yet.

Source: ReactionGIFs.us

19. When you’ve been working for 6 months on a complicated closing and at the last second, the seller tells you they’re backing out of the deal.

Farley Reaction
Source: ReactionGIFs.us

20. When you’re stuck on the phone with a prospect who feels the need to tell you their life story.

Source: ReactionGIFs.us

21. When you miss out on the deal of a lifetime.

Source: ReactionGIFs.us

When you realize that ALL investors experience pain in their journey, and only the most successful ones have the strength to endure adversity.

Source: reddit.com

Photo: alles-schlumpf

About Author

Seth Williams

Seth Williams (@retipsterseth , G+) is an experienced land investor, commercial real estate banker and residential income property owner. He is also the Founder of REtipster.com - a real estate investing blog providing real world guidance for part time real estate investors.


    • Thanks Sara – I know I’ve experienced at least half of these myself (unfortunately, it wasn’t difficult for me to think of the nasty situations we investors can get ourselves into). I guess we all have to experience some of the lows along with the highs.

  1. Melodee Lucido on

    omgosh Seth I NEEDED this to have a good laugh (through tears) this morning. Number 19 is the one that wins the prize for me this week. I’m saving this for comic relief.

    The last one though makes it all worth it.

    Thank you so much >>> sometimes we just gotta laugh

  2. Seth,

    After a long Sunday of hard work, and weeks of not taking days off, just when I was about to bang my head against the wall again until I felt no pain, I read your posting. The best reading I had in a while….It made my night….Number 21 is my favorite…lol! Thank you very much…Take care, Pedro.

  3. Seth, Number 19 for sure! Just lost a deal that was laid out for the seller and definitely the buyer! Thought it could not go wrong! This is the first time i have laughed since that happened two weeks ago! But the rest are so truthful and yet so funny! Thanks, I needed that!

    Steve Dinges

  4. Too funny Seth, loving the animated GIFs. The one about Home Depot is what happens to my partner after we come back from what we call Bunnings here in Australia. Lol. They’re all hilarious but #12, wow – those eyes! haha. And yes, #20 – I agree.

  5. #14. No contest.
    Does anyone but a realtor’s kid understand what’s it’s like to be on a Sunday afternoon ride through the mountains and hearing “Look! An open house!”?
    Don’t get me wrong; looking around vacant houses was fun — it was those awful words “you kids stay in the car this time. We’ll only be a few minutes”.
    At minimum half an hour (more likely 45 min) sitting in a hot car, bored, with ABSOLUTELY nothing to do.
    Oh well. Here I am cruising around on Bigger Pockets, so I guess it all paid off in the end…

  6. Rofl man… I haven’t used rofl in probably 6 years! I laughed hard at #14, but when I read #17 I started to cry I was cracking up so hard hahah my wife was in the other room and asked if I was crying.

    #18 was soo good too.

    Always love reading these references you make. Keep it up bro!

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