How to Exit a Real Estate Deal Gone Bad

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I’m pretty sure that every real estate deal we go into looks rosy in the beginning. The numbers look good, the property looks good, the market looks good, and the cash flow looks good.

Then maybe some time goes by, and you’re standing there wondering what went wrong. I know I’ve been there. While it could be the case where we made an error in judgement when entering into the investment, often something changes that’s outside of our control.

So, what are those possible changes, and how do we stay on top of them?

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Evaluating Your Portfolio

Regardless of what you invest in, I think it’s prudent to periodically evaluate your portfolio.

I review both my properties and my notes at least on a quarterly basis. My notes are probably easier since I get statements from my mortgage servicer, and I only invest in performing notes on a personal basis. As for my real estate, I have a property manager also send me monthly statements with everything collected and all the expenses we’ve encountered broken down, so that part is pretty easy.

When it comes to portfolio analysis, though, it’s really up to us as investors to adjust our strategy when needed. For example, my mortgage servicer doesn’t tell me the best time to sell a note. Maybe it’s best to sell when equity is up in the marketplace, when there’s more than 12 or 24 months of payment history, when there’s less than a certain number of payments remaining, or when you’ve already collected back your initial investment. You get the idea.

Well, it can work similarly for real estate. For me, I look at my properties’ location, cash flow, condition, appreciation potential, insurance expenses, taxes, and aggravation level at least yearly. (Does anyone look at aggravation levels besides me? This can include the level of difficulty for renting it out.) I also look for strategies to increase profitability and cash flow, if possible.

To be honest, in over 25 years of owning rentals, I’ve had almost everything that can negatively impact a piece of real estate happen to me. I’ve had property values drop. I’ve put three kitchens in the same unit in a 10-year period. I’ve had abandoned cars, units burn down, tenants get incarcerated, and even an attempted murder in one of my units. I’ve had a SWAT team and the DEA destroy units. I’ve had natural disasters like floods and trees crashing through the unit.


Related: 5 Smart Exit Strategies for Buy & Hold Investors Looking to Get Out of the Game

But, I’ve also had good times too, with many good tenants staying over 10 years.

It’s a numbers game that comes with the territory. Like Tony Robbins says, “It’s not about resources, it’s about resourcefulness.” Sure it helps to have reserves, but it’s not about what happens to us as landlords, but how we react to what happens.

Oftentimes, I look at my properties to figure out how I can improve things. For example, I may renovate or add a bedroom to increase rents. Maybe I’ll rent the garage separately or drop a prefab garage on the property. I’ve even built garages on a lot behind one of my multi-units, which dramatically increased the value and appreciation potential.

I’ve also taken out lines of credit on rentals to tap into the equity and use it to reinvest in other real estate deals, but I mostly use it to do hard money deals for fellow rehabbers and to buy notes. I really hate to see all that equity (from market appreciation and from paying down of the mortgage) just sitting there idle and underutilized.

Pulling Off the Band-Aid

Sometimes the property has just turned into a loser. Maybe the cash flow is down due to higher taxes and township inspection fees. Or maybe the maintenance is so high because it’s an older property that’s becoming a money pit. I had a property once where the flood insurance got so high it just wasn’t worth keeping. Sometimes you can no longer make lemonade out of lemons, and it’s time to cut your losses.

There are other times when I look less at how the individual property is doing and more at how the entire portfolio is looking, especially if they are good properties in good areas.

It’s not necessarily a bad strategy to have your high cash flow, low value (or appreciating) properties help pay for the good properties. I have a good friend whose note portfolio’s cash flow helps to maintain his real estate portfolio. This strategy can work really well in some places like California, where real estate may not cash flow as well but has a lot of potential appreciation.


How You Leave the Party

But how you exit the deal can be just as important as the investment you choose. Sometimes it is how we sell that makes the biggest difference.

I remember my mom had three houses that by retirement had doubled in value. They cash flowed alright, but mom was sick of the ongoing maintenance and management. (To be quite honest, I was getting tired of hearing about it, too.)

Related: What’s Your Exit Strategy? A Case for Converting Your Real Estate to Paper Assets

So, we sold the properties with special terms to other real estate investors. We carried a second mortgage for five years, interest only, with a seller’s assist, and this allowed the buyers to take over mom’s properties with no cash out-of-pocket. Plus, the properties still cash flowed for them.

Mom didn’t have to pay any real estate commissions, she got out of the maintenance business, and she continued to cash flow (from the notes) on properties she no longer owned. She no longer had earned income in retirement, so she didn’t miss the little bit of remaining depreciation very much. This was a great way to exit, and it worked very well for all parties.

In addition to selling with terms like mom did, there are also other strategies available. If you’re not cash flowing enough but there’s significant equity, you could increase your yield by refinancing and reinvesting that capital (as I mentioned before) in something that cash flows more. Of course, you can sell the property. If you take a loss, you may be able to offset other gains somewhere else in your portfolio. That being said, deciding upon the right strategy is really up to the individual and depends on their situation.

I’m curious to hear from some BP folks – what’s the turning point for you that means its time walk away from a deal? What is your favorite strategy for leaving the party?

Let me know with a comment!

About Author

Dave Van Horn

Dave Van Horn is President at PPR The Note Co. - an operating entity that manages several funds that buy/sell/hold residential mortgages, both performing and delinquent. Dave has been in the Real Estate business for over 25 years, starting out as a Realtor and contractor and moving onto everything from fix and flips to Raising Private Money.


  1. Curt Smith

    Good question! And yes like your mother’s seller financing comes to mind as one of the best ways to exit a marginal deal. I’m financing to occupants using a Licensed Loan Mortgage Originator staying under 3 per year (12 months rolling). Or you can finance to an investor as many times as you want without the need of a LMLO and any terms you both agree to. This path requires less fix up if any vs trying to sell retail via an agent. This 2nd path has many more costs and risk that you’ll net out more than just seller financing as-is.

    • Dave Van Horn

      Hi Curt,

      Thanks for commenting. Not sure I understand what you mean by your last sentence, can you clarify? Specifically I’m not clear on how the 2nd path has more costs and risks while simultaneously netting more profit?

      In the scenario I listed, it was a commercial loan so I didn’t have any Dodd Frank/LLMO issues, it was low cost since I ran it through my title company and because my mother’s properties doubled in value, the new buyer’s 1st mortgage more than eliminated any risk. Also, it may be a riskier deal selling to the general public but I knew and trusted the investor buyers.

  2. Mark Pace

    I own several single family rentals in an area of expensive properties. Due to appreciation I am now selling these properties using a 1031 tax free exchange and reinvesting into a less expensive market about an hour away. I can sell one property and replace it with two properties that greatly increase my cash flow. I use a property manager and not concerned the properties are 50 miles away. I have never seen a rental market as hot as we have in Florida. It is not unusual to have multiple called the first day on the market.

  3. Robyn J.

    Dave –
    I also enjoy reading your posts.
    I have several ‘loaded’ rentals for sale now. I initially bought all but one as a NP note; rehabbed & have rented. But since rentals are not my biz plan I want to sell. Like your mom I would prefer to sale to investors wanting cash flowing deals. What/where do you think is the best source to market these? I am willing on most of them to carry paper.

    • Dave Van Horn

      Thanks Robyn!

      You might have luck posting these properties on the BP Marketplace here:

      I would also suggest marketing these deals via social media channels (there are plenty of groups on LinkedIn and Facebook where you can post properties for sale). You could also try marketing in person at your local REIA. In the pre-internet days, I would always push out deals to my local network of Real Estate Investors at these meetings. I always say, if the deal is good enough a buyer will find you.


      • Robyn J.

        Thanks Dave.
        I’m in Texas so my local club doesn’t have any interested in out of state rentals (nice group but typical want to be able to drive by their investments). I have posted on BP. Guess I need to do that more frequently. Thanks again.

        • Dave Van Horn

          Hi Robyn,

          Have you thought about marketing to the REIA group(s) where the properties are located? Posting on these local groups’ Facebook/LinkedIn page may be a good idea as well, if you can’t attend these meetings often in person.

          Or you could find an investor friendly Realtor/REO Realtor in these markets to push out these properties to their lists.


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